Methyl chloroformate → Hydrochloric Acid

HRID 18374Notes

Reaction equation

HRID 18374 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[N:8]=[CH:9][N:10]([CH3:12])[CH:11]=1)[C:3]([OH:5])=[O:4].C([O-])(O)=O.[Na+].[Cl:18][C:19]([O:21][CH3:22])=[O:20]>>[CH3:22][O:21][C:19]([NH:1][C@@H:2]([CH2:6][C:7]1[N:8]=[CH:9][N:10]([CH3:12])[CH:11]=1)[C:3]([OH:5])=[O:4])=[O:20].[ClH:18]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 921051-Methyl-L-histidineHCID 516892Sodium Bicarbonate

Product 2

HCID 313Hydrochloric AcidYield 748.4%HCID 66769205(s)-2-(Methoxycarbonylamino)-3-(1-methyl-1h-imidazol-4-yl)propanoic acid

Procedure

Cap-127 was prepared according to the method for Cap-126 above starting from (S)-2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid (1. II g, 6.56 mmol), NaHCO3 (1.21 g, 14.4 mmol) and ClCO2Me (0.56 mL, 7.28 mmol). The title compound was obtained as its HCl salt (1.79 g, >100%) contaminated with inorganic salts. LCMS and 1H NMR showed the presence of ca. 5% of the methyl ester. The crude mixture was used as is without further purification. 1HNMR (400 MHz, CD3OD) δ 8.90 (s, 1H), 7.35 (s, 1H), 4.48 (dd, J=5.0, 8.6 Hz, 1H), 3.89 (s, 3H), 3.62 (s, 3H), 3.35 (m, 1H), 3.08 (m, 1H); LCMS: Anal. Calcd. for C9H13N3O4: 227.09. found: 228 (M+H)+.

Workup

  1. customCap-127 was prepared

Sources & evidence

ORD record
ord-214e78876ace43b486aeb7d2a1835d49
Source dataset
uspto-grants-2010_06
Patent number
US07741347B2

Reaction notes

Loading…