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Triethylamine → (RS,SR)-2-(benzenesulfonyl-fluoro-methylcarbamoyl-methyl)-6-chloro-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester

HRID 602808
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HRID 602808 반응식
[C:1]1([S:7]([C:10]([CH:16]2[CH2:28][CH2:27][C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([Cl:29])[CH:24]=4)[NH:19][C:18]=3[CH2:17]2)([F:15])[C:11]([NH:13][CH3:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[O:37](C(OC(C)(C)C)=O)[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:41]([O:40][C:38]([N:19]1[C:18]2[CH2:17][CH:16]([C:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:8])=[O:9])([F:15])[C:11](=[O:12])[NH:13][CH3:14])[CH2:28][CH2:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[C:23]([Cl:29])[CH:24]=2)=[O:37])([CH3:44])([CH3:43])[CH3:42]
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 11270482(RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-methyl-acetamide

생성물 1

HCID 67267476(RS,SR)-2-(benzenesulfonyl-fluoro-methylcarbamoyl-methyl)-6-chloro-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester수율 78.5%

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매

실험 절차

0.924 g (0.002 mol) of (RS, SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-methyl-acetamide were dissolved in 20 mL CH2Cl2 at RT. Then, 0.59 mL triethylamine (0.004 mol, 2 eq), 26 mg DMAP (0.2 mmol, 0.1 eq) and 0.556 g BOC2O (0.003 mol, 1.2 eq) were added. The reaction mixture was stirred for 2H30. The reaction was quenched with a saturated NH4Cl aqueous solution, and the product extracted with CH2Cl2. The combined organic phases were dried on Na2SO4, filtered and evaporated. The crude material was precipitated in diethyl ether. The solvent was removed and the remaining solid was dried under vaccum to yield to 0.840 g (74%) of (RS, SR)-2-(benzenesulfonyl-fluoro-methylcarbamoyl-methyl)-6-chloro-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester as a white solid, MS: 552 (MNH4+).

후처리

  1. customThe reaction was quenched with a saturated NH4Cl aqueous solution
  2. extractionthe product extracted with CH2Cl2
  3. customThe combined organic phases were dried on Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material was precipitated in diethyl ether
  7. customThe solvent was removed
  8. customthe remaining solid was dried under vaccum

출처 및 근거

ORD 기록
ord-ccabb7dbfe3c4c09b06617d08c10f088
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07906546B2

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