Hydrochloric Acid → 2-(2-Amino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxy)imino acetic acid, hydrochloride salt

HRID 1732289Notes

Reaction equation

HRID 1732289 reaction equation
[ClH:1].[C:2]1([CH:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:9][C:10]([C:12]([CH3:28])([O:14][N:15]=[C:16]([C:20]2[N:21]=[C:22]([NH:25]C=O)[S:23][CH:24]=2)[C:17]([OH:19])=[O:18])[CH3:13])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[ClH:1].[NH2:25][C:22]1[S:23][CH:24]=[C:20]([C:16](=[N:15][O:14][C:12]([C:10]([O:9][CH:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:11])([CH3:28])[CH3:13])[C:17]([OH:19])=[O:18])[N:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 538511182-(1-Diphenylmethoxycarbonyl-1-methylethoxy)imino-2-(2-formamido-4-thiazolyl)acetic acid

Product 1

HCID 898850052-(2-Amino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxy)imino acetic acid, hydrochloride salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (403 μl., 4.84 mmol.) is added to a suspension of the product from part (d) (1.7 g., 3.64 mmol.) in dry methanol. The suspended material dissolves immediately and the reaction mixture is stirred for four hours. The solvent is removed under reduced pressure yielding as a residue 2-(2-amino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxy)imino acetic acid, hydrochloride salt: NMR (CDCl3 -CD3OD) δ 1.70 (s,6H,CH3), 6.93 (s, 1H, thiazole H), 7.02 (s, 1H, CHO), 7.33 (s, 10H, aromatic H).

Workup

  1. dissolutionThe suspended material dissolves immediately
  2. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-5007754357d94fb8858930d31a0ded76
Source dataset
uspto-grants-1980_12
Patent number
US04237128

Reaction notes

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