Sodium → HCID 44209962, compound

HRID 1534799Notes

Reaction equation

HRID 1534799 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][C:6]1([OH:33])[CH2:11][CH:10]2[C:12]([CH3:14])([CH3:13])[C:7]1([CH2:15][S:16]([N:19]1[CH2:24][CH2:23][C:22]3([C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25]3)[CH2:21][CH2:20]1)(=[O:18])=[O:17])[CH2:8][CH2:9]2)C.[Na]>CO.O>[CH3:1][O:3][C:4](=[O:34])[CH2:5][C:6]1([OH:33])[CH2:11][CH:10]2[C:12]([CH3:14])([CH3:13])[C:7]1([CH2:15][S:16]([N:19]1[CH2:24][CH2:23][C:22]3([C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25]3)[CH2:21][CH2:20]1)(=[O:17])=[O:18])[CH2:8][CH2:9]2

Participants

5

Reactant 2

HCID 5360545SodiumHCID 76480054HCID 76480054, compound

Product 1

HCID 44209962HCID 44209962, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

(1S(1.Alpha.,2α,4α))-2-hydroxy-7,7-dimethyl-1-((spiro(1H-indene-1,4'-piperidin)-1'-yl sulfonyl)methyl)bicyclo(2.2.1)heptane-2-acetic acid ethyl ester (45 mg, 0.092 mmol) was stirred in a mixture of methanol (1 ml) and water (1 ml) and treated with sodium hxdroxide (0.1 ml of a 5N solution in water; 0.5 mmol). The mixture was stirred for 1 hr at ambient temperature, then evaporated to dryness in vacuo. The residue was treated with saturated sodium bicarbonate solution and extracted with ether. The ether layer was evaporated to dryness in vacuo and the residue was chromatographed on a silica gel column eluted with 15% EtOAc in hexane. The product fractions were evaporated to dryness in vacuo, and the residue was triturated with CH2Cl2 and again evaporated to dryness. The residue was dried in vacuo at ambient temperature overnight to give the title compound: (mp 81°-83°).

Workup

  1. customevaporated to dryness in vacuo
  2. additionThe residue was treated with saturated sodium bicarbonate solution
  3. extractionextracted with ether
  4. customThe ether layer was evaporated to dryness in vacuo
  5. customthe residue was chromatographed on a silica gel column
  6. washeluted with 15% EtOAc in hexane
  7. customThe product fractions were evaporated to dryness in vacuo
  8. customthe residue was triturated with CH2Cl2
  9. customagain evaporated to dryness
  10. customThe residue was dried in vacuo at ambient temperature overnight

Sources & evidence

ORD record
ord-6bb7029953194ceca2f71f2d798c928b
Source dataset
uspto-grants-1992_02
Patent number
US05091387

Reaction notes

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