Methanol → HCID 86587153, compound

HRID 895703Notes

Reaction equation

HRID 895703 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, 0.22H), 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, 2.8H), 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-3a0ecf60bd93462a925d6ad38a24126a
Source dataset
uspto-grants-2005_07
Patent number
US06916850B2

Reaction notes

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