Diethyl Ether → HCID 86643604, compound

HRID 2381036Notes

Reaction equation

HRID 2381036 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C@@H:4]([NH:25]C(OC(C)(C)C)=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:16])[NH:14][CH3:15])=[C:8]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=1.C(OCC)C.[Cl:39]CCl>O1CCOCC1>[Cl-:39].[CH2:18]([O:17][C:8]1[CH:7]=[C:6]([CH2:5][C@H:4]([NH3+:25])[C:3]([O:2][CH3:1])=[O:33])[CH:11]=[CH:10][C:9]=1[O:12][C:13](=[O:16])[NH:14][CH3:15])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 68727062HCID 68727062, compound

Product 1

HCID 86643604HCID 86643604, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-3-(3-benzyloxy-4-methylcarbamoyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (0.90 g) in dichloromethane (12 ml) cooled with an ice-bath was added 4 MHCl in dioxane (6 ml). The mixture was stirred at 0° C. for 2 h. Diethyl ether was added and a white solid was precipitated. (S)-2-(3-Benzyloxy-4-methylcarbamoyloxy-phenyl)-1-methoxycarbonyl-ethyl-ammonium chloride was obtained as white solid by filtration, 0.83 g. 1H NMR (400 MHz, d6-DMSO) 2.64 (s, 3H), 3.10 (m, 2H), 3.68 (s, 3H), 4.33 (m, 1H), 5.10 (s, 2H), 6.79 (m, 1H), 7.04-7.12 (m, 2H), 7.32-7.45 (m, 5H), 7.60 (m, 1H), 8.64 (s, 3H).

Workup

  1. customa white solid was precipitated

Sources & evidence

ORD record
ord-b0bd8bea3b4740128bb4957f3d17a97e
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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