Benzyl chloroformate → HCID 54272252, compound

HRID 2212615Notes

Reaction equation

HRID 2212615 reaction equation
[NH2:1][CH2:2][C@@H:3]([OH:5])[CH3:4].Cl[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]>C1C=CC=CC=1>[CH2:10]([O:9][C:7]([NH:1][CH2:2][C@@H:3]([OH:5])[CH3:4])=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 7311736(S)-(+)-1-Aminopropan-2-ol

Product 1

HCID 54272252HCID 54272252, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of (S)-1-amino-2-propanol (9.76 g, 130 mmol) in anhydrous benzene (60 mL) at 0° C. was added benzyl chloroformate (10.23 g, 60 mmol) in anhydrous benzene (120 mL) slowly, in portions, over a period of 20 min while vigorously stirring under an atmosphere of nitrogen. The mixture was stirred for 1 hour at 0° C., then allowed to warm to room temperature and stirred for a further 2 hours. The mixture was washed with water (2×) and brine (2×) before the organic layer was dried over anhydrous MgSO4. Evaporation of all solvent gave the title product as an oil. 1H NMR (CDCl3) δ1.22 (d, 3H,) 2.40 (bs, 1H), 3.07 (m, 1H), 3.37 (m, 1H) ), 3.94 (m, 1H), 5.16 (s, 2H), 5.27 (m, 1H), 7.38 (m, 5H). MS m/z (electrospray) 232 [M+23]+ (100%), 166 (96).

Workup

  1. stirringThe mixture was stirred for 1 hour at 0° C.
  2. stirringstirred for a further 2 hours
  3. washThe mixture was washed with water (2×) and brine (2×) before the organic layer
  4. dry with materialwas dried over anhydrous MgSO4
  5. customEvaporation of all solvent

Sources & evidence

ORD record
ord-33e914cefeb14603b68b3404293794b2
Source dataset
uspto-grants-2006_09
Patent number
US07102013B2

Reaction notes

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