1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Boc-Gly-Gly-Ala-Pro-OBzl

HRID 440231Notes

Reaction equation

HRID 440231 reaction equation
[NH:1]([C:25]([O:27]C(C)(C)C)=O)[CH2:2][C:3]([NH:5][C@H:6]([C:8]([N:10]1[CH2:24][CH2:23][CH2:22][C@H:11]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:9])[CH3:7])=[O:4].Cl.O1CCOCC1.[NH:39]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40]C(O)=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>>[NH:39]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][C:25]([NH:1][CH2:2][C:3]([NH:5][C@H:6]([C:8]([N:10]1[CH2:24][CH2:23][CH2:22][C@H:11]1[C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])=[O:9])[CH3:7])=[O:4])=[O:27]

Participants

6

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 14656486Boc-Gly-Ala-Pro-OBzl2×HCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 131719402Boc-Gly-Gly-Ala-Pro-OBzlYield 85.9%

Procedure

Compound II (65.03 g, 0.15 mole) was deblocked with HCl/dioxane and coupled to Boc-Gly-OH (26.3 g, 0.15 mole) using EDCI with HOBt in the same manner as that described for II to give 63.2 g (yield 85.9%) of III Rf1, 0.3; Rf2, 0.46.

Sources & evidence

ORD record
ord-bba9ca61a2634869bafebecd68ef9fdd
Source dataset
uspto-grants-1996_05
Patent number
US05519004

Reaction notes

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