Hydrochloric Acid → glycine N-(2-(N-(phenylmethoxycarbonyl)sarcosylamino)ethyl)amide hydrochloride

HRID 53089Notes

Reaction equation

HRID 53089 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]([CH2:13][C:14]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:38])[CH2:21][NH:22]C(=O)[C@H](CC(C)C)NC(OC(C)(C)C)=O)=[O:15])[CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(COC(N(CC(NCCNC(=O)CNC(OC(C)(C)C)=O)=O)C)=O)C=CC=CC=1.[ClH:69].O>ClCCl>[ClH:69].[C:1]1([CH2:7][O:8][C:9]([N:11]([CH2:13][C:14]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:38])[CH2:21][NH2:22])=[O:15])[CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 67628369HCID 67628369, compoundHCID 131719971HCID 131719971, compound

Product 1

HCID 19961349glycine N-(2-(N-(phenylmethoxycarbonyl)sarcosylamino)ethyl)amide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(N-(1,1-Dimethylethoxycarbonyl)leucyl)glycine N-(2-(N-(phenylmethoxycarbonyl)sarcosylamino)ethyl)amide. N-(1,1-Dimethylethoxycarbonyl)glycine N-(2-(N-(phenylmethoxycarbonyl)sarcosylamino)ethyl)amide (5.22 g, 8 mmol) was treated with excess hydrogen chloride in dichloromethane (50 mL) for 1 h. Water (50 mL) was added and the mixture was stirred vigorously for 15 min. The solvent and excess reagent were evaporated from the aqueous layer under reduced pressure to give crude glycine N-(2-(N-(phenylmethoxycarbonyl)sarcosylamino)ethyl)amide hydrochloride as a white solid. This material was stirred with N,N-diisopropylethylamine (3.231 g, 25 mmol) and N-(1,1-dimethylethoxycarbonyl)leucine 2,4,5-trichlorophenyl ester (3.19 g, 7.8 mmol) (Example II, Intermediate A) in dimethylformamide (30 mL) for 3 d. The solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and was washed with aqueous sodium hydroxide (5%), aqueous sulphuric acid (10%) and water and was dried with anhydrous magnesium sulphate. Evaporation of the solvent under reduced pressure gave N-(N-(1,1-dimethylethoxycarbonyl)leucyl)glycine N-(2-(N-(phenylmethoxycarbonyl)sarcosylamino)ethyl)amide (3.26 g, 78%).

Workup

  1. customThe solvent and excess reagent were evaporated from the aqueous layer under reduced pressure

Sources & evidence

ORD record
ord-733410222e30474ab661df595a04538d
Source dataset
uspto-grants-1997_04
Patent number
US05618528

Reaction notes

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