Water → HCID 58246723, compound

HRID 451735Notes

Reaction equation

HRID 451735 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:9]([OH:11])[CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.[CH3:27][S:28](Cl)(=[O:30])=[O:29].O>C(Cl)Cl>[CH:1]1([CH2:7][C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:9]([O:11][S:28]([CH3:27])(=[O:30])=[O:29])[CH3:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59382828HCID 59382828, compound

Product 1

HCID 58246723HCID 58246723, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl (2S,3R)-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate (0.44 g, 1.62 mmol) in dry CH2Cl2 (10 mL) was added Et3N (0.71 g, 7 mmol, 4 eq) at 0 to −5° C. A solution of methanesulfonyl chloride (0.8 g, 7 mmol, 2 eq) in dry CH2Cl2 (5 mL) was added dropwise at the same temperature. The mixture was allowed to warm to rt gradually. TLC showed that the starting material had disappeared. Water (30 mL) was added. The aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers was washed with 10% aq citric acid, satd aq NaHCO3 and brine, then dried over Na2SO4, filtered and concentrated to give tert-butyl (2S,3R)-1-cyclohexyl-3-(methanesulfonyloxy)butan-2-yl-carbamate (0.46 g, 81%), which was used in the next step without purification.

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  2. washThe combined organic layers was washed with 10% aq citric acid
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7bceccfe7eb041058234a9374e78c05e
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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