1,2-Dichloroethane → HCID 59753476, compound

HRID 751757Notes

Reaction equation

HRID 751757 reaction equation
[CH2:1]([O:8][C:9](=[O:13])[C@H:10]([CH3:12])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[C:28]([N:35]1[CH2:43][CH2:42][CH2:41][CH2:40][CH:36]1[C:37](O)=[O:38])([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].CN1CCOCC1>C1CCCCC1.C(OCC)(=O)C.C1(C)C=CC=CC=1.O.CN(C)C=O>[CH2:1]([O:8][C:9]([C@@H:10]([NH:11][C:37]([C@@H:36]1[CH2:40][CH2:41][CH2:42][CH2:43][N:35]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:38])[CH3:12])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 5818311-[(Tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 726858benzyl (2S)-2-aminopropanoate

Product 1

HCID 59753476HCID 59753476, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

9.85 g (45.57 mmol) of alanine benzyl ester, 6.79 g of HOBT (50.23 mmol) and 10.07 g (52.52 mmol) of EDC are introduced into dimethylformamide (30 ml) at 0° C., treated with 10.47 g (45.67 mmol) of N-Boc-pipecolic acid. and 27.71 g (274 mmol) of N-methylmorpholine and stirred overnight at room temperature. Subsequently, the mixture is treated with water and toluene, the phases are separated and the organic phase is washed with sat. aqueous sodium chloride solution. 14.9 g (83% of th.) of product are isolated by means of silica gel chromatography using cyclohexane/ethyl acetate 10/1.

Workup

  1. customthe phases are separated
  2. washthe organic phase is washed with sat. aqueous sodium chloride solution
  3. custom14.9 g (83% of th.) of product are isolated by means of silica gel chromatography

Sources & evidence

ORD record
ord-e366dc8162114663a1d3e9ffb8c7a364
Source dataset
uspto-grants-2008_07
Patent number
US07405201B2

Reaction notes

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