Dicyclohexylcarbodiimide → Benzyl 3-[N-(1-(S)-ethoxycarbonyl-3phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(R)-carboxylate

HRID 1651439Notes

Reaction equation

HRID 1651439 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([OH:20])=O)[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].ON1C2C=CC=CC=2N=N1.[C:31]1([C:37]2[S:41][CH:40]([C:42]([O:44][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[O:43])[NH:39][N:38]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([N:39]1[N:38]=[C:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[S:41][C@@H:40]1[C:42]([O:44][CH2:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)=[O:43])=[O:20])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 5702571N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanineHCID 13773249HCID 13773249, compound

Product 1

HCID 13773251Benzyl 3-[N-(1-(S)-ethoxycarbonyl-3phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(R)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A stirred mixture of N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanine (3.1 g) and 1-hydroxybenzotriazole (1.7g) in dichloromethane (100ml) was treated with a solution of the product of step (a) (6.85g) in dichloromethane (25ml). A solution of dicyclohexylcarbodiimide (2.26g) in dichloromethane (20ml) was added over 20 minutes and the mixture was stirred at room temperature for 2 days under nitrogen.

Sources & evidence

ORD record
ord-5445dd6ca2954e948601577ca24be249
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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