Hydrochloric Acid → HCID 57979792, compound

HRID 1868024Notes

Reaction equation

HRID 1868024 reaction equation
[OH:1][C@H:2]([CH3:16])[CH2:3][NH:4][CH2:5][C@@H:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:7].C(N(C(C)C)CC)(C)C.Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].Cl>ClCCl>[C:11]([O:10][C:9]([NH:8][C@@H:6]([CH3:7])[CH2:5][N:4]([CH2:3][C@H:2]([OH:1])[CH3:16])[C:27](=[O:28])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:15])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 57979784HCID 57979784, compound

Product 1

HCID 57979792HCID 57979792, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of tert-butyl (S)-1-[(R)-2-hydroxypropylamino]propan-2-ylcarbamate (3.0 g, 12.93 mmol) and diisopropylethylamine (3.38 mL, 19.4 mmol) in anhydrous dichloromethane (100 mL) at 0° C. was added benzyl chloroformate (2.65 g, 15.5 mmol). After stirring at 0° C. for 1 hour, the cooling bath was removed and the reaction mixture was allowed to stir at room temperature for an additional 45 minutes. Reaction was complete as determined by TLC. The reaction mixture was added with 1N HCl and extracted with dichloromethane. Organic layer washed with water then brine and it was dried over MgSO4. Solvent evaporation afforded benzyl {(2S)-2-[(tert-butoxycarbonyl)amino]propyl}[(2R)-2-hydroxypropyl]carbamate in 84.5% yield (3.95 g) as colorless gummy oil.

Workup

  1. customthe cooling bath was removed
  2. stirringto stir at room temperature for an additional 45 minutes
  3. customReaction
  4. extractionextracted with dichloromethane
  5. washOrganic layer washed with water
  6. dry with materialbrine and it was dried over MgSO4
  7. customSolvent evaporation

Sources & evidence

ORD record
ord-5e04ca8b882541108bc6ba951d9b0afc
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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