Triethylamine → HCID 69301956, compound

HRID 987061Notes

Reaction equation

HRID 987061 reaction equation
[CH2:1]([NH:8][C:9]([CH2:11][CH:12]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:13][CH:14]([OH:36])[CH2:15][CH2:16][CH:17]1[CH:26]2[C:21](=[CH:22][CH:23]([CH3:34])[CH2:24][CH:25]2[O:27][C:28](=[O:33])[CH:29]([CH3:32])[CH2:30][CH3:31])[CH:20]=[CH:19][CH:18]1[CH3:35])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>CS(C)=O>[CH2:1]([NH:8][C:9]([CH2:11][CH:12]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:39])[CH3:40])[CH2:13][C:14](=[O:36])[CH2:15][CH2:16][CH:17]1[CH:26]2[C:21](=[CH:22][CH:23]([CH3:34])[CH2:24][CH:25]2[O:27][C:28](=[O:33])[CH:29]([CH3:32])[CH2:30][CH3:31])[CH:20]=[CH:19][CH:18]1[CH3:35])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 13713138HCID 13713138, compound

Product 1

HCID 69301956HCID 69301956, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred solution of 2.9 g (4.6 mmol) 2-methyl-butyric acid 8-[6-benzylcarbamoyl-5-(tert.-butyl-dimethyl-silanyloxy)-3-hydroxy-hexyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester and 5.2 ml (37 mmol) triethyl amine in 22 ml DMSO is added a solution of 4.4 g (28 mmol) SO3.pyridine complex in 22 ml DMSO. After 2 hours at room temperature the mixture is poured on ice and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent evaporated. The residue is chromatographed over silica gel (hexane/ethyl acetate 9/1 to 7/3) to afford 2-methyl-butyric acid 8-[6-benzylcarbamoyl-5-(tert.-butyl-dimethyl-silanyloxy)-3-oxo-hexyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester as an oil. MS (FAB) m/z 630 ([M+Li]+).

Workup

  1. additionAfter 2 hours at room temperature the mixture is poured on ice
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. customthe solvent evaporated
  5. customThe residue is chromatographed over silica gel (hexane/ethyl acetate 9/1 to 7/3)

Sources & evidence

ORD record
ord-8c652777f0ba44a6811be2bf7e89b051
Source dataset
uspto-grants-2003_10
Patent number
US06630492B1

Reaction notes

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