Skip to main content
. 2013 Dec 2;53(3):851–855. doi: 10.1002/anie.201307987

Table 3.

Microflow amide bond formation with various substrates. Inline graphic

Entry Structure of Cond. Yield [%]
desired product (desired) (epimer)
1 Inline graphic flow A[a] batch[d] 92 57 1 2
2 Inline graphic flow B[b] batch[d] quant. 40 <1 <1
3 Inline graphic flow B[b] batch[d] 92 75 2 17
4 Inline graphic flow A[a] batch[d] 94 71 <1 1
5 Inline graphic flow C[c] batch[d] 97 74 3 18
6 Inline graphic flow B[b] batch[d] 89 47 <1 1
7 Inline graphic flow A[a] batch[d] 80 58 <1 1
8 Inline graphic flow A[a] batch[d] 74 53 <1 <1
9 Inline graphic flow A[a] batch[d] 98 <28 <1
[a]

 Carboxylic acid: 2.5 equiv, triphosgene: 0.4 equiv.

[b]

Carboxylic acid: 3.0 equiv, triphosgene: 0.5 equiv.

[c]

Carboxylic acid: 2.5 equiv, triphosgene: 0.4 equiv, DIEA: 2.5 equiv, solvent A: MeCN, reaction temperature: 10 °C.

[d]

Reaction time for the activation of carboxylic acid and the amidation: 30 s. Fmoc=9-fluorenylmethyloxycarbonyl.