Carbodiimide → HCID 12944666, compound

HRID 1284043Notes

Reaction equation

N=C=N.[NH:4](C(OCC1C=CC=CC=1)=O)[C@H:5]([C:10](O)=[O:11])[C@H:6]([CH2:8][CH3:9])[CH3:7].[NH2:23][C@H:24]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[NH2:4][C@H:5]([C:10]([NH:23][C@H:24]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:11])[C@H:6]([CH2:8][CH3:9])[CH3:7]

Participants

Reactant 3

HCID 160435Carbodiimide

HCID 2724772N-[(Phenylmethoxy)carbonyl]-L-isoleucine

HCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoate

Product 1

HCID 12944666HCID 12944666, compoundYield 90%

Procedure

In accordance with the carbodiimide method indicated Z-Ile-OH (4) was linked with H-Phe-OtBu (5). By means of subsequent catalytic diacylation of the intermediate benzyloxy-carbonyl-dipeptide ester (4-5a) it was possible to isolate H-Ile-Phe-OtBu (4-5b) with a yield of above 90 %.

Sources & evidence

ORD record: ord-425d11d6661a418e8f82938d2e3df9b6
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03978035

Reaction notes

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