Water → (S)-1-phenyl-1-(tert-butoxycarbonylamino)-2-(1-trifluoroacetylindoline-5-sulfonyl)aminoethane

HRID 508138Notes

Reaction equation

HRID 508138 reaction equation
[C:1]1([C@H:7]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][N:9]=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:20][C:21]([F:38])([F:37])[C:22]([N:24]1[C:32]2[C:27](=[CH:28][C:29]([S:33](Cl)(=[O:35])=[O:34])=[CH:30][CH:31]=2)[CH2:26][CH2:25]1)=[O:23].O>ClCCl.[Pd]>[C:1]1([C@H:7]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][NH:9][S:33]([C:29]2[CH:28]=[C:27]3[C:32](=[CH:31][CH:30]=2)[N:24]([C:22](=[O:23])[C:21]([F:38])([F:20])[F:37])[CH2:25][CH2:26]3)(=[O:34])=[O:35])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 110883061-(Trifluoroacetyl)-2,3-dihydro-1H-indole-5-sulfonyl chlorideHCID 86762376HCID 86762376, compound

Product 1

HCID 117641850(S)-1-phenyl-1-(tert-butoxycarbonylamino)-2-(1-trifluoroacetylindoline-5-sulfonyl)aminoethane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

A mixture of (S)-2-phenyl-2-tert-butoxycarbonylaminoethylazide (10.50 g, 0.04 mol) dissolved in 250 mL dichloromethane and 2.5 g of 10% Pd/C was hydrogenated for 5 hrs at 70 psi of H2. The catalyst was separated by filtration. To the filtrate triethylamine (8 mL) was added, the mixture was cooled to −20° C. followed by slow addition of 1-(trifluoroacetyl)indoline-5-sulfonyl chloride (12.56 g, 0.04 mol) dissolved in 150 mL dichloromethane. The reaction mixture was then stirred overnight at room temperature. Water (500 mL) was added and the mixture was shaken well, organic layer was separated, shaken with 200 mL 2% citric acid, separated and dried with MgSO4. The drying agent was separated by filtration. The filtrate was concentrated and the title product was precipitated by addition of hexane. Yield: 17.67 g, (86%); (MH)+=514; 1H NMR (DMSO-d6): 1.33 (s, 9H), 2.85-2.99 (m, 2H), 3.26-3.30 (t, J=8.0 Hz, 2H), 4.31-4.35 (t, J=8.0 Hz, 2H), 4.53-4.59 (m, 1H), 7.19-7.35 (m, 6H), 7.66-7.68 (m, 2H), 7.72-7.75 (t, J=6.0 Hz, 1H), 8.13-8.15 (d, J=8.8 Hz, 1H).

Workup

  1. customThe catalyst was separated by filtration
  2. additionTo the filtrate triethylamine (8 mL) was added
  3. stirringthe mixture was shaken well
  4. customorganic layer was separated
  5. stirringshaken with 200 mL 2% citric acid
  6. customseparated
  7. dry with materialdried with MgSO4
  8. customThe drying agent was separated by filtration
  9. concentrationThe filtrate was concentrated
  10. customthe title product was precipitated by addition of hexane

Sources & evidence

ORD record
ord-d3ff2208c9044d21b4420877514a093f
Source dataset
uspto-grants-2015_08
Patent number
US09095575B2

Reaction notes

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