Triethylamine → (S)-2-(((Benzyloxy)carbonyl)amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl methanesulfonate

HRID 426069Notes

Reaction equation

HRID 426069 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][O:7][CH2:6]1.C(N(CC)CC)C.[S:29](Cl)([CH3:32])(=[O:31])=[O:30]>C(Cl)Cl>[CH3:32][S:29]([O:1][CH2:2][C@@H:3]([NH:11][C:12]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:21])[CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][O:7][CH2:6]1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59364340Benzyl ((S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)carbamate

Product 1

HCID 59364367(S)-2-(((Benzyloxy)carbonyl)amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl methanesulfonateYield 138.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl (5)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate (26 g, 69.99 mmol) and triethylamine (21.21 g, 210 mmol) in CH2Cl2 at 0° C. was added mesyl chloride (16.1 g, 140 mmol) dropwise. The reaction mixture was stirred at room temperature until the staring material disappeared. The reaction was quenched with ice-cold water, extracted with CH2Cl2 (3×100 ml), washed with water (3×50 ml), dried over Na2SO4, and concentrated in vacuo to give the product (36 g), which was used for the next step without purification.

Workup

  1. customThe reaction was quenched with ice-cold water
  2. extractionextracted with CH2Cl2 (3×100 ml)
  3. washwashed with water (3×50 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8db068ac91a14600b6f35dbd85d8692d
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

Loading…