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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
Notes
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Reaction equation

HRID 602808 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344DichloromethaneSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-ccabb7dbfe3c4c09b06617d08c10f088
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07906546B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes