Triethylamine → HCID 11283868, compound

HRID 2250817Notes

Reaction equation

HRID 2250817 reaction equation
C(N(CC)CC)C.[Si:8]([O:15][C@@H:16]([CH3:37])[C@@H:17]([OH:36])[CH2:18][CH2:19][C:20]1[C:25]2[N:26]=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[O:28][C:24]=2[CH:23]=[CH:22][CH:21]=1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[CH3:38][S:39]([O:36][C@H:17]([C@@H:16]([O:15][Si:8]([C:11]([CH3:14])([CH3:12])[CH3:13])([CH3:10])[CH3:9])[CH3:37])[CH2:18][CH2:19][C:20]1[C:25]2[N:26]=[C:27]([C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)[O:28][C:24]=2[CH:23]=[CH:22][CH:21]=1)(=[O:41])=[O:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11236178HCID 11236178, compound

Product 1

HCID 11283868HCID 11283868, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Triethylamine (0.248 ml) was added to an ice-cooled solution of (3S,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-4-benzoxazolyl]-pentan-3-ol (P0006; 0.40 g) and methanesulfonyl chloride (0.139 ml) in dichloromethane (13 ml) and the mixture was stirred at 5° C. for 30 min. The mixture was washed with water, dried and evaporated. The residual oil (494 mg) was chromatographed over silica gel (15 g) eluting with a mixture of hexane and dichloromethane (2:1) to dichloromethane to give a colorless oil of (3S,4S)4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-4-benzoxazolyl]-3-pentyl methanesulfonate (P0007; 372 mg).

Workup

  1. washThe mixture was washed with water
  2. customdried
  3. customevaporated
  4. customThe residual oil (494 mg) was chromatographed over silica gel (15 g)
  5. washeluting with a mixture of hexane and dichloromethane (2:1) to dichloromethane

Sources & evidence

ORD record
ord-4ef7cd84675148f79b3d2ed591708e73
Source dataset
uspto-grants-2008_01
Patent number
US07317107B2

Reaction notes

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