Bromopinacolone → HCID 86645971, compound

HRID 1094316Notes

Reaction equation

HRID 1094316 reaction equation
FC(F)(F)C1N=C(NC2C=CC([C@@H](C)C(O)=O)=CC=2)SC=1.[C:22]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([C@@H:32]([CH3:37])[C:33]([O:35]C)=[O:34])=[CH:28][CH:27]=1)(=[S:24])[NH2:23].Br[CH2:39][C:40](=O)[C:41]([CH3:44])([CH3:43])[CH3:42]>>[C:41]([C:40]1[N:23]=[C:22]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C@@H:32]([CH3:37])[C:33]([OH:35])=[O:34])=[CH:28][CH:27]=2)[S:24][CH:39]=1)([CH3:44])([CH3:43])[CH3:42]

Participants

4

Reactant 3

HCID 21642BromopinacoloneHCID 86645968HCID 86645968, compoundHCID 86645970HCID 86645970, compound

Product 1

HCID 86645971HCID 86645971, 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 1-bromopinacolone (1.13 ml, 8.40 mmol). The following acid hydrolysis afforded the pure (2R)-2-{4-[(4-tert-butyl-1,3-thiazol-2-yl)amino]phenyl}propanoic acid (1.41 g, 4.62 mmol) as pale yellow oil (55%). 1H-NMR (CDCl3): δ 8.30 (bs, 1H, NH), 7.40 (d, 2H, J=7 Hz), 7.20 (d, 2H, J=7 Hz), 6.40 (s, 1H), 3.75 (q, 1H, J=7 Hz), 1.50 (d, 3H, J=7 Hz), 1.40, (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-652427ad59df46b29b7457b84c5f6445
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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