Dichloromethane → HCl 4-amino-3-methylbenzoyl methionine methyl ester

HRID 1739132Notes

Reaction equation

HRID 1739132 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[N:5]([C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([CH3:21])[CH:15]=1)C(OC(C)(C)C)=O.C(Cl)[Cl:29]>>[ClH:29].[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([CH3:21])[CH:15]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 67566381N-BOC-4-amino-3-methylbenzoyl methionine methyl ester

Product 1

HCID 67565931HCl 4-amino-3-methylbenzoyl methionine methyl esterYield 96.6%

Procedure

N-BOC-4-amino-3-methylbenzoyl methionine methyl ester (0.99 g, 2.59 mmol) was dissolved in CH2Cl2 (15-20 ml) and precipitated with 3M HCl/Et2O (20.7 ml). 0.83 g (96.6%) of pale orange precipitate was obtained after drying overnight on the vacuum pump. mp 157-159° C.; 1H NMR (CD3OD) 2.04 (3H,s), 2.11-2.25 (1H, m), 2.47 (3H, s), 2.52-2.68 (3H. m), 3.74 (3H, s), 4.75-4.80 (1H, m), 7.48 (1H, d, J=8.2 Hz), 7.81 (2H, d, J=8.2 Hz), 7.87 (1H, s); 13C NMR (CD3OD) 15.23, 17.28, 31.43, 31.51, 52.91, 53.37, 124.41, 127.85, 131.99, 133.63, 134.14, 135.65, 169.05, 173.84; anal. calc. for C14H21N2O3S, C: 50.52, H: 6.36, N: 8.42; found C: 50.71, H: 6.40, N: 8.34.

Workup

  1. customprecipitated with 3M HCl/Et2O (20.7 ml)

Sources & evidence

ORD record
ord-0afafb50499d4a5597d6109f647ee370
Source dataset
uspto-grants-1999_10
Patent number
US05965539

Reaction notes

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