Methanesulfonyl chloride → HCID 59271892, compound

HRID 1893211Notes

Reaction equation

[CH2:1]([N:3]([CH:11]([C:19]1[NH:20][C:21](=[O:37])[C:22]([OH:36])=[C:23]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[O:26])[N:24]=1)[CH2:12][CH2:13][C@H:14]([O:17][CH3:18])[CH2:15][OH:16])[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2].[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(C#N)(C)=O.C(Cl)Cl.O>[CH3:38][S:39]([O:37][C:21]1[C:22]([O:36][S:39]([CH3:38])(=[O:41])=[O:40])=[C:23]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[O:26])[N:24]=[C:19]([CH:11]([N:3]([C:4]([O:5][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:10])[CH2:1][CH3:2])[CH2:12][CH2:13][C@H:14]([O:17][CH3:18])[CH2:15][O:16][S:39]([CH3:38])(=[O:41])=[O:40])[N:20]=1)(=[O:41])=[O:40]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of tert-butyl ethyl[(4S)-1-(4-{[(4-fluorobenzyl)amino]carbonyl}-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)-5-hydroxy-4-methoxypentyl]carbamate (30 g, 57.4 mmol) in AcCN (500 mL) at 0° C. was added TEA (48 mL, 344 mmol) followed by a dropwise addition of a solution of MsCl (22.37 mL, 287 mmol) in DCM (15 mL). The resulting mixture was stirred at 0° C. for 30 minutes, then diluted with H2O (˜100 mL) and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was used in the next step without further purification. LC-MS: 757.5 (M+1).

Workup

extractionextracted with EtOAc (3×)
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was used in the next step without further purification

Sources & evidence

ORD record: ord-938e93f053d64312af40feb50e4e4178
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513234B2

Reaction notes

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