Dicyclohexylcarbodiimide → Z-Thr-Pro-OtBu

HRID 1680051Notes

Reaction equation

HRID 1680051 reaction equation
[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@H:2]([C:6]([OH:8])=O)[C@@H:3]([CH3:5])[OH:4].[NH:19]1[CH2:30][CH2:29][CH2:28][C@H:20]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@H:2]([C:6]([N:19]1[CH2:30][CH2:29][CH2:28][C@H:20]1[C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])=[O:8])[C@@H:3]([CH3:5])[OH:4]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 88217N-((Benzyloxy)carbonyl)-L-threonineHCID 6453108L-Proline 1,1-dimethylethyl ester

Product 1

HCID 131712253Z-Thr-Pro-OtBuYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In the way described in B(1), 0.33 mol Z-Thr-OH and 0.35 mol H-Pro-OtBu are coupled with the aid of HOBt and DCCI in DMF. Yield 64%; melting point 65°-67° C. The Z-Thr-Pro-OtBu obtained in this way is hydrogenated in the way described above (see B.3.b.).

Sources & evidence

ORD record
ord-8a64b2cbc55043c8adcb6e87a248f493
Source dataset
uspto-grants-1981_06
Patent number
US04271152

Reaction notes

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