Triethylamine → HCID 86611173, compound

HRID 1946987Notes

Reaction equation

HRID 1946987 reaction equation
C(N(CC)CC)C.[C:8]([CH:15]([CH3:19])[C@H:16]([NH2:18])[OH:17])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[C:8]([CH:15]([CH3:19])[C@:16]([NH2:18])([S:21]([CH3:20])(=[O:23])=[O:22])[OH:17])([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86611174HCID 86611174, compound

Product 1

HCID 86611173HCID 86611173, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DCM (400 mL) and triethylamine (83.9 mL, 0.60 mol) were added to a flask containing (R)-2-boc-amino-propan-1-ol. The reaction mixture was cooled in an ice bath for 30 min, and methanesulfonyl chloride (37.0 mL, 0.478 mol) was added dropwise over a five min period. The resulting mixture was stirred for 1 hour, the ice bath removed, and the mixture stirred for 18 h at RT. The resulting mixture was washed with aqueous NaOH (10%), and the organic layer dried over MgSO4, filtered, and concentrated under reduced pressure to give (R)-2-boc-amino-1-methanesulfonyl-propan-1-ol (91.93 g).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath for 30 min
  2. customthe ice bath removed
  3. stirringthe mixture stirred for 18 h at RT
  4. washThe resulting mixture was washed with aqueous NaOH (10%)
  5. dry with materialthe organic layer dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b21ce1564d04d489a2373cb1bcfbf70
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

Loading…