N2 [(1,1-dimethylethoxycarbonyl]-N6-[(phenylmethoxy)carbonyl]-(R)-6-[(phenylmethoxy)carbonyl]-L-lysyl]-D-Alanine Phenylmethyl Ester → HCID 67798175, compound
Reaction equation
N#N.[C:3]1([CH2:9][O:10][C:11](=[O:51])[C@@H:12]([CH3:50])[NH:13][C:14](=[O:49])[C@@H:15]([CH2:24][CH2:25][CH2:26][CH:27]([C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:40])[NH:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[NH:16]C(OC(C)(C)C)=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)(C(F)(F)F)=O>[C:3]1([CH2:9][O:10][C:11](=[O:51])[C@@H:12]([CH3:50])[NH:13][C:14](=[O:49])[C@@H:15]([CH2:24][CH2:25][CH2:26][CH:27]([C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:40])[NH:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[NH2:16])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Participants
3
Procedure
A solution of 40b (251 mg, 0.37 mmol) in TFA (870 μl) is stirred for 30 min at 0° C. The TFA is removed and the oil is taken up in EtOAc and washed with saturated NaHCO3 solution. Drying and removal of the solvent gives 3b (225 mg, slight excess) which is used in subsequent reactions without further handling: NMR δ 1.39 (d, 3 H) and 1.20-1.70 (overlapping m, 4 H), 1.82 (br s, 2 H), 3.23 (br s, variable, 2 H), 3.33 (br s, 1 H), 4.39 (m, 1 H), 4.47 (apparent quintet, 1 H), 5.03-5.13 (m, 6 H), 5.27 (br d, 1 H), 7.35 (m, 15 H), 7.95 (br d, 1 H) ; MS (FAB) m/z 576 (M+H), 598 (M+Na).