Dichloromethane → HCID 20737862, 화합물

HRID 354271노트

반응식

HRID 354271 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1)=[O:7])([CH3:4])(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O.C(Cl)(OCC1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44]2[C:39]1=[CH:40][CH:41]=[CH:42][CH:43]=2)=O>CCOCC>[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:22][CH:23]=1)([O:5][CH2:1][CH:4]1[C:43]2[C:44](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:45]2[C:50]1=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:7]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 343679-Fluorenylmethyl chloroformateHCID 69332259HCID 69332259, 화합물

생성물 1

HCID 20737862HCID 20737862, 화합물수율 91%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To the above (S)-4-(1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxybenzoic acid was added CH2Cl2 (10 mL) and TFA (10 mL). The mixture was stirred at room temp for 1 hr Et2O was added to the mixture and resulting solid was collected. The solid was dissolved in water (100 mL), dioxane (50 mL) and NaHCO3 (4.4 g). Fmoc-Cl (3.34 g, 12.9 mmol) was added to the solution, and the resulting mixture was stirred for 20 hr at room temp. The mixture was washed with Et2O (×2) and aqueous layer was separated. The layer was acidified by the addition of 1 N HCl. The mixture was extracted with EtOAc. The extract was washed with water, brine, dried over MgSO4 and evaporated in vacuo to afford 5.36 g (91%) (S)-4-(1-Fmoc-2-pyrrolidinyl)methoxybenzoic acid as a viscous oil, which was crystallized on standing.

후처리

  1. additionwas added to the mixture
  2. customresulting solid
  3. customwas collected
  4. dissolutionThe solid was dissolved in water (100 mL)
  5. washThe mixture was washed with Et2O (×2) and aqueous layer
  6. customwas separated
  7. additionThe layer was acidified by the addition of 1 N HCl
  8. extractionThe mixture was extracted with EtOAc
  9. washThe extract was washed with water, brine
  10. dry with materialdried over MgSO4
  11. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-a4e517fd80e64206b12915c996ed5959
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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