Methanesulfonyl chloride → HCID 89315659, compound

HRID 1497278Notes

Reaction equation

HRID 1497278 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:14]2[NH:15][C:16](=[O:18])[O:17][C@H:13]2[CH2:12][C@H:11]([CH2:19][OH:20])[C@H:10]1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>N1C=CC=CC=1.[NH4+].[Cl-]>[CH3:29][S:30]([O:20][CH2:19][C@@H:11]1[C@@H:10]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@H:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@H:14]2[NH:15][C:16](=[O:18])[O:17][C@H:13]2[CH2:12]1)(=[O:32])=[O:31]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 71152541HCID 71152541, compound

Product 1

HCID 89315659HCID 89315659, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of (3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-(hydroxymethyl)hexahydrobenzo[d]oxazol-2(3H)-one (1.86 g, 4.86 mmol) in pyridine (11 mL) at −20° C. was added MeSO2Cl (0.723 g, 6.31 mmol). The mixture was slowly warmed to room temperature and stirred for 4 h. The reaction was diluted with aqueous saturated NH4Cl (100 mL) and extracted with EtOAc (2×60 mL). The extracts were washed with 0.5 N HCl (3×60 mL), dried with MgSO4. The solvent was evaporated to give ((3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-2-oxooctahydrobenzo[d]oxazol-6-yl)methyl methanesulfonate as a white solid (2.25 g, 100%) which was pure enough for next reaction. MS m/z 484.1 (M+23, 100%); 1H NMR (400 MHz, CDCl3) δ 7.30-7.44 (m, 10H), 4.92 (d, J=11.9 Hz, 1H), 4.87 (d, J=11.1 Hz, 1H), 4.66-4.70 (m, 2H), 4.65 (d, J=11.0 Hz, 1H), 4.57 (d, J=11.9 Hz, 1H), 4.43 (dd, J=9.7 Hz, 4.2 Hz, 1H), 4.21 (dd, J=9.7 Hz, 3.0 Hz, 1H), 3.59 (t, J=6.8 Hz, 1H), 3.51 (t, J=7.6 Hz, 1H), 3.41 (t, J=8.9 Hz, 1H), 2.12-2.26 (m, 2H), 1.79-1.87 (m, 1H).

Workup

  1. extractionextracted with EtOAc (2×60 mL)
  2. washThe extracts were washed with 0.5 N HCl (3×60 mL)
  3. dry with materialdried with MgSO4
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ff6e18dfb0624306bb3a6bc664fd784f
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

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