Potassium Carbonate → HCID 11661118, compound

HRID 269738Notes

Reaction equation

HRID 269738 reaction equation
C([O:4][C@@H:5]1[CH2:9][CH2:8][C@H:7]([CH2:10][C:11]([NH:13][C:14]2[S:15][C:16]3[C:22]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:21][CH:20]=[C:19]([O:29][CH3:30])[C:17]=3[N:18]=2)=[O:12])[CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].C[O-].[Na+]>CO>[OH:4][C@@H:5]1[CH2:9][CH2:8][C@H:7]([CH2:10][C:11]([NH:13][C:14]2[S:15][C:16]3[C:22]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:21][CH:20]=[C:19]([O:29][CH3:30])[C:17]=3[N:18]=2)=[O:12])[CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10942334Sodium MethoxideHCID 86602720HCID 86602720, compound

Product 1

HCID 11661118HCID 11661118, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(cis)-2-(3-Acetoxy-cyclopentyl)-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-acetamide (first eluting isomer, 64 mg, 0.15 mmol), potassium carbonate (82 mg, 0.59 mmol) and sodium methoxide (5.4M in methanol, 1.37 ul, 0.0074 mmol) are stirred together in methanol (6 ml) for 4 h at ambient temperature. Evaporation of the solvent, dissolution in methylene chloride and extraction with saturated sodium carbonate afforded, after drying and evaporation of the methylene chloride, a crude material. After crystallization from diethyl ether, the title compound was obtained as light yellow crystals (91% yield). MS: m/e=392(M+H+), mp 168-171° C., α589=−4.87 (CH2Cl2, c=1.1%).

Workup

  1. customEvaporation of the solvent, dissolution in methylene chloride
  2. extractionextraction with saturated sodium carbonate
  3. customafforded
  4. customafter drying
  5. customevaporation of the methylene chloride
  6. customAfter crystallization from diethyl ether

Sources & evidence

ORD record
ord-ad664a119dc04e65a47b53ecff0f1d6f
Source dataset
uspto-grants-2008_11
Patent number
US07449461B2

Reaction notes

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