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. Author manuscript; available in PMC: 2014 Sep 1.
Published in final edited form as: Medchemcomm. 2013 Jul 15;4(9):10.1039/C3MD00134B. doi: 10.1039/C3MD00134B

Table 3.

Synthesis of N3-acylated 7.

graphic file with name nihms514349u2.jpg

entry R acylating reagent 6 yieldc 7 yieldc
1 Me 3a 6a 83 7a 48
2 Et 3b 6b 84 7b 44
3 Pr 3c 6c 85 7c 37
4 iPr 3d 6d 67 7d 40
5 TBSO(CH2)4 3e 6e 62 7e 50
6 graphic file with name nihms514349t3.jpg 3f 6f 56 7f 25
a

This step was carried out with compound 5 (1.0 equiv) and an anhydride in neat or an NHS ester (1.5 equiv) in DMF.

b

This operation was executed with 6 (1.0 equiv), BOP (1.3 equiv) and DBU (1.5 equiv) for 4 h. Then NH3 (7 N in MeOH) was added.

c

Isolated yields.