Acetic Acid → HCID 53785838, compound

HRID 1108160Notes

Reaction equation

HRID 1108160 reaction equation
CN(C)C(=O)[S:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C@H:17]3[CH2:21][O:20][C:19]([C:22]4[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=4[F:29])=[N:18]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.CO.C[O-].[Na+].C(O)(=O)C>O>[F:28][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([F:29])[C:22]=1[C:19]1[O:20][CH2:21][C@H:17]([C:14]2[CH:13]=[CH:12][C:11]([C:8]3[CH:9]=[CH:10][C:5]([SH:4])=[CH:6][CH:7]=3)=[CH:16][CH:15]=2)[N:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 21968652HCID 21968652, compound

Product 1

HCID 53785838HCID 53785838, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.60 g of (S)-S-[4'-[2-(2,6-difluorophenyl)-4,5-dihydro-4-oxazolyl][1,1'-biphenyl]-4-yl] dimethylcarbamothioate, 5 mL of methanol, and 0.30 g of 25% NaOMe solution was heated at 60° C. for 7 h and allowed to stand at ambient temperature for 3 d. After adding 0.5 mL of acetic acid and 5 mL of water, the product was filtered, washed with water, and suction-dried to afford 0.30 g of product, m.p. 133-135° C. The 1H NMR (CDCl3) spectrum was the same as that of the racemic product of Example 5.

Workup

  1. filtrationthe product was filtered
  2. washwashed with water
  3. customsuction-dried

Sources & evidence

ORD record
ord-10c2047ea4734449a462f85c9b7aeedb
Source dataset
uspto-grants-2000_05
Patent number
US06063932

Reaction notes

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