Chloroform → HCID 10665296, compound

HRID 2234823Notes

Reaction equation

HRID 2234823 reaction equation
[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].C1CCC(N=C=NC2CCCCC2)CC1.[CH:31](Cl)(O)[CH:32]([Cl:34])[Cl:33].C(Cl)(Cl)[Cl:38]>CN(C1C=CN=CC=1)C>[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([O:5][CH2:31][C:32]([Cl:34])([Cl:38])[Cl:33])=[O:4]

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 10868DicyclohexylcarbodiimideHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 1194271,1,2-Trichloroethanol

Product 1

HCID 10665296HCID 10665296, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Boc-Pro-OH (6.46 g, 30.0 mmol) in a 300 ml short neck flask was dissolved in distilled CHCl3 (80 ml). DCC (6.82 g, 33.0 mmol) dissolved in advance in a minimum quantity of distilled CHCl3 in ice bath with stirring was added thereto, and trichloroethanol (3.50 ml, 37.0 mmol) and DMAP (0.38 g, 3.0 mmol) was further added, and the mixture was stirred in an ice bath for 2 hours and at room temperature all day. After filter-out of DCUrea, the filtrate was subjected to vacuum concentration. The residue was dissolved in AcOEt, was sequentially washed with a 10% aqueous citric acid solution, water, a saturated aqueous NaHCO3 solution, water, and saturated saline, and was dried with Na2SO4. The filtrate was subjected to vacuum concentration to yield an oil-form product.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred in an ice bath for 2 hours and at room temperature all day
  3. filtrationAfter filter-out of DCUrea
  4. concentrationthe filtrate was subjected to vacuum concentration
  5. dissolutionThe residue was dissolved in AcOEt
  6. washwas sequentially washed with a 10% aqueous citric acid solution, water
  7. dry with materiala saturated aqueous NaHCO3 solution, water, and saturated saline, and was dried with Na2SO4
  8. concentrationThe filtrate was subjected to vacuum concentration
  9. customto yield an oil-form product

Sources & evidence

ORD record
ord-47a9cb95990545e781cca9dd1e0690b5
Source dataset
uspto-grants-2010_05
Patent number
US07713926B2

Reaction notes

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