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Dimethylamine → Phenylmethyl (2S,4R)-2-[(dimethylamino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate

HRID 1581713
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HRID 1581713 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[C:17]([OH:19])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C1CC[CH:33]([N:36]=[C:37]=NC2CCCCC2)CC1.CNC>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[C:17]([N:36]([CH3:37])[CH3:33])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 674DimethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

생성물 1

HCID 16123358Phenylmethyl (2S,4R)-2-[(dimethylamino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate수율 78.8%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

A mixture of 15 g of (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid, 7.64 g of HOBT and 11.65 g of DCC in 250 ml of DCM is stirred for 1 hour at RT. The reaction mixture is cooled on an ice bath, dimethylamine gas is added by sparging for 10 minutes and this mixture is stirred for 3 hours at RT. An insoluble material is filtered off and the filtrate is concentrated under vacuum. The residue is taken up in saturated Na2CO3 solution and extracted with DCM, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum. 13 g of the expected product are obtained in the form of an oil.

후처리

  1. temperatureThe reaction mixture is cooled on an ice bath
  2. customby sparging for 10 minutes
  3. stirringthis mixture is stirred for 3 hours at RT
  4. filtrationAn insoluble material is filtered off
  5. concentrationthe filtrate is concentrated under vacuum
  6. extractionextracted with DCM
  7. dry with materialthe organic phase is dried over Na2SO4
  8. customthe solvent is evaporated off under vacuum

출처 및 근거

ORD 기록
ord-bd5c175ef4a047df8f9d4d9cb951712c
출처 데이터셋
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06730695B2

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