Water → HCID 59383020, compound

HRID 451862Notes

Reaction equation

HRID 451862 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C@H:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:17][OH:18])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:34][S:35](Cl)(=[O:37])=[O:36].O>C(Cl)Cl>[CH3:34][S:35]([O:18][CH2:17][C@@H:16]([NH:19][C:20]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:26])[CH2:15][CH:12]1[CH2:11][CH2:10][CH:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2])[CH2:14][CH2:13]1)(=[O:37])=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59382972HCID 59382972, compound

Product 1

HCID 59383020HCID 59383020, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-(4-(tert-butyldimethylsilyloxy)cyclohexyl)-3-hydroxypropan-2-ylcarbamate (101.6 g, 0.263 mol) and Et3N (66.3 g, 0.656 mol) in CH2Cl2 (500 mL) was added MsCl (66.1 g, 0.577 mol) at −20° C., which was allowed stir for 1 h at rt. The reaction mixture was treated with water (300 mL) and extracted with CH2Cl2 (3×100 mL). The organic layers dried over Na2SO4 and evaporated give (S)-2-(tert-butoxycarbonylamino)-3-(4-(tert-butyldimethylsilyloxy)cyclohexyl)propyl methanesulfonate (121 g, 99%).

Workup

  1. extractionextracted with CH2Cl2 (3×100 mL)
  2. dry with materialThe organic layers dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-aaa83a4d82ad479ea4192d3f98dc5447
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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