Chloroacetaldehyde → HCID 86645972, compound

HRID 1094317Notes

Reaction equation

HRID 1094317 reaction equation
FC(F)(F)[C:3]1[N:4]=[C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)[S:6][CH:7]=1.C(NC1C=CC([C@@H](C)C(OC)=O)=CC=1)(=S)N.ClCC=O>>[S:6]1[CH:7]=[CH:3][N:4]=[C:5]1[NH:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 33ChloroacetaldehydeHCID 86645968HCID 86645968, compoundHCID 86645970HCID 86645970, compound

Product 1

HCID 86645972HCID 86645972, compoundYield 55%

Procedure

The acid was obtained following the same procedure described for (2R)-2-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanoic acid and starting from methyl (2R)-2-[4-(carbamothioylamino)phenyl]propanoate (2.0 g, 8.40 mmol) and chloroacetaldehyde (50 wt. % in H2O, 0.54 ml, 8.40 mmol). The following acid hydrolysis afforded the pure (2R)-2-{4-[(1,3-thiazol-2-yl)amino]phenyl}propanoic acid (1.47 g, 5.62 mmol) as pale yellow oil (55%). 1H-NMR (CDCl3): δ 8.30 (bs, 1H, NH), 8.10 (d, 1H, J=2.5 Hz), 7.50 (d, 1H, J=2.5 Hz) 7.40 (d, 2H, J=7 Hz), 7.20 (d, 2H, J=7 Hz), 3.75 (q, 1H, J=7 Hz), 1.50 (d, 3H, J=7 Hz),

Workup

  1. customThe acid was obtained
  2. customThe following acid hydrolysis

Sources & evidence

ORD record
ord-ba159daf7bfa4d3e90604e7dcf12c470
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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