Triethylamine → HCID 86611173, compound

HRID 1818729Notes

Reaction equation

HRID 1818729 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

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

Workup

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

Sources & evidence

ORD record
ord-aadae683bbca4929a5c2a389306ac166
Source dataset
uspto-grants-2009_10
Patent number
US07601726B2

Reaction notes

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