Hydrochloric Acid → HCID 86643600, compound

HRID 2381033Notes

Reaction equation

HRID 2381033 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C@@:4]([N:30]=C=O)(OC(C)(C)C)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]([O:20][C:21](=[O:24])[NH:22][CH3:23])[CH:7]=1.[ClH:34].C(OCC)C>ClCCl>[Cl-:34].[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C@H:4]([NH3+:30])[C:3]([O:2][CH3:1])=[O:33])=[CH:7][C:8]=1[O:20][C:21](=[O:24])[NH:22][CH3:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86643602HCID 86643602, compound

Product 1

HCID 86643600HCID 86643600, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-(4-Benzyloxy-3-methylcarbamoyloxy-phenyl)-2-tert-butoxy-carbonylamino-propionic acid methyl ester (0.80 g) in dichloromethane (10 ml) was added HCl solution (4M in dioxane, 4 ml) at 0° C. The mixture was stirred at this temperature for 2 h. Diethyl ether was added and a white solid precipitated. (S)-2-(4-Benzyloxy-3-methylcarbamoyloxy-phenyl)-1-methoxycarbonyl-ethyl-ammonium chloride was obtained by filtration as a white solid, 0.654 g. 1H NMR (400 MHz, d6-DMSO) 2.65 (d, 3H), 3.01-3.14 (m, 2H), 3.67 (s, 3H), 4.24 (m, 1H), 5.10 (s, 2H), 7.01-7.11 (m, 3H), 7.30-7.44 (m, 5H), 7.61 (m, 1H), 8.64 (br, 3H).

Workup

  1. customa white solid precipitated

Sources & evidence

ORD record
ord-a7ac11f8fcce4dfb99822778b585d4f6
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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