Chloroacetone → HCID 86645969, compound

HRID 1094315Notes

Reaction equation

HRID 1094315 reaction equation
F[C:2](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)C>>[CH3:2][C:3]1[N:4]=[C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([C@@H:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:13][CH:14]=2)[S:6][CH:7]=1

Participants

4

Reactant 3

HCID 6571ChloroacetoneHCID 86645968HCID 86645968, compoundHCID 86645970HCID 86645970, compound

Product 1

HCID 86645969HCID 86645969, compoundYield 75%

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 chloro-2-propanone (0.67 ml, 8.40 mmol). The following acid hydrolysis afforded the pure (2R)-2-{4-[(4-methyl-1,3-thiazol-2-yl)amino]phenyl}propanoic acid (1.65 g, 6.30 mol) as a yellow oil (75%). 1H-NMR (CDCl3): δ 8.15 (bs, 1H, NH), 7.40 (d, 2H, J=7 Hz), 7.20 (d, 2H, J=7 Hz), 6.35 (s, 1H), 3.75 (q, 1H, J=7 Hz), 2.18, (s, 3H), 1.50 (d, 3H, J=7 Hz).

Workup

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

Sources & evidence

ORD record
ord-b287a65c404f4932af54936105e5ff5d
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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