Triethylamine → (2S,3S)-2-benzyloxy-5-(1-naphthyl)-3-pentyl methanesulfonate

HRID 278484Notes

Reaction equation

[CH2:1]([O:8][C@H:9]([C@@H:11]([OH:24])[CH2:12][CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].C(N(CC)CC)C>ClCCl>[CH3:25][S:26]([O:24][C@@H:11]([CH2:12][CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[C@@H:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:10])(=[O:28])=[O:27]

Participants

Conditions

Temperature: 4 °C

Procedure

To an ice-cooled solution of (2S,3S)-2-benzyloxy-5-(1-naphthyl)pentan-3-ol (obtained in Preparation 26) (7.43 g) in dichloromethane (100 ml) was added methanesulfonyl chloride (2.15 ml) followed by triethylamine (3.88 ml). The mixture was stirred at 4° C. for 40 min. After being diluted with dichloromethane, the mixture was washed with water and brine, dried and concentrated in vacuo to give (2S,3S)-2-benzyloxy-5-(1-naphthyl)-3-pentyl methanesulfonate (9.92 g, 107.4%) as an oil. The product was used directly in the next step without further purification.

Workup

washthe mixture was washed with water and brine
customdried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a20ce673e54e486cb67530a62c074fd5
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06359145B1

Reaction notes

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