Methanol → HCID 86587153, compound

HRID 2183569Notes

Reaction equation

HRID 2183569 reaction equation
[NH2:1][CH:2]([CH2:6][CH2:7][C:8](=[O:28])[NH:9][CH:10]([C:21](=[O:27])[NH:22][CH2:23][C:24]([OH:26])=[O:25])[CH2:11][S:12][CH2:13][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:15])[C:3](O)=[O:4].[C:29]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:40][OH:41]>>[CH3:40][O:41][C:3](=[O:4])[CH:2]([NH2:1])[CH2:6][CH2:7][C:8](=[O:28])[NH:9][CH:10]([C:21](=[O:27])[NH:22][CH2:23][C:24]([O:26][CH3:29])=[O:25])[CH2:11][S:12][CH2:13][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 10295709HCID 10295709, compound

Product 1

HCID 86587153HCID 86587153, compound

Procedure

A mixture of 2-Amino-4-[1-(carboxymethyl-carbamoyl)-2-(2-ethoxycarbonyl-2-oxo-ethylsulfanyl)-ethylcarbamoyl]-butyric acid (200 mg) and p-toluenesulfonic acid (30 mg) in methanol (100 mL) was heated to reflux for 72 h. The solvent was then evaporated and the residue was dried under high vacuum to afford the desired product, 2-amino-4-[2-(2-ethoxycarbonyl-2-oxo-ethylsulfanyl)-1-(methoxycarbonylmethyl-carbamoyl)-ethylcarbamoyl]-butyric acid methyl ester, as a yellowish sticky solid. 1H-NMR (D3COD, 300 MHz) δ (ppm): 6.24 (d, J=10.5 Hz, 0.22 H), 4.49-4.4.33 (m, 1H), 4.15-3.91 (m, 3H), 3.76 (s, 3H), 3.65-3.57 (m, 2H), 3.51 (s, 3H), 3.21-2.73 (m, 2.8 H), 2.45-2.43 (m, 2H), 2.10-1.92 (m, 2H), 1.13-1.03 (m, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 72 h
  3. customThe solvent was then evaporated
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-5204274b5176428f8cae7b4613c3ddaf
Source dataset
uspto-grants-2005_05
Patent number
US06900218B2

Reaction notes

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