Hydrochloric Acid → HCID 131722824, compound

HRID 649727Notes

Reaction equation

HRID 649727 reaction equation
[NH:1]([C:24]([O:26]C(C)(C)C)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].Cl.N[C@H](C(N[C@H](C(OCC=C)=O)CC1C=CC=CC=1)=O)[C@H](CC)C.[N:55]1([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:62][CH2:61][CH2:60][C@H:56]1C(O)=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[N:55]1([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:62][CH2:61][CH2:60][C@H:56]1[C:24]([NH:1][C@H:2]([C:7]([NH:9][C@H:10]([C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4])=[O:26]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131722825HCID 131722825, compoundHCID 131722826HCID 131722826, compound

Product 1

HCID 131722824HCID 131722824, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After cleavage of the Boc group from Boc-Ile-Phe-Oallyl according to general procedure D, the HCl salt of Ile-Phe-Oallyl was coupled to Boc-Pro in DMF (60 ml) via general procedure C, by using TEA (1.94 ml, 13.9 mmol), HOBt (3.047 g, 19.9 mmol), and EDCl (2.79 g. 14.6 mmol). After workup, the product was crystallized from cold EthOAc to give the title compound in 73% yield as a white solid. Rf=0.30 (50% EthOAc/hexane). [α]D23=−60.5 (c 0.585, CHC3). FABMS (C28H41N3O6) found 516.3 (M+H+).

Workup

  1. customAfter workup, the product was crystallized from cold EthOAc

Sources & evidence

ORD record
ord-15e7c2cd25b949f9a9406f8723230515
Source dataset
uspto-grants-2001_08
Patent number
US06270957B1

Reaction notes

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