Water → HCID 86618247, compound

HRID 1159801Notes

Reaction equation

HRID 1159801 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[CH:18][N:19]3[S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:10][CH:9]1[C:33](O)=[O:34])=O)(C)(C)C.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37].O>C1COCC1>[F:39][C:38]([F:41])([F:40])[C:36]([OH:42])=[O:37].[F:39][C:38]([F:41])([F:40])[C:36]([OH:42])=[O:37].[C:27]1([S:24]([N:19]2[C:20]3[C:16](=[C:15]([CH2:14][N:11]4[CH2:12][CH2:13][NH:8][CH:9]([CH2:33][OH:34])[CH2:10]4)[CH:23]=[CH:22][CH:21]=3)[CH:17]=[CH:18]2)(=[O:26])=[O:25])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 68716901HCID 68716901, compound2×

Product 1

HCID 86618247HCID 86618247, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1M BH3 in THF (0.2 mL, 0.2 mmol) was added dropwise to a solution of 1-(tert-butoxycarbonyl)-4-{[1-(phenylsulfonyl)-1H-indol-4-yl]methyl}piperazine-2-carboxylic acid (0.010 g, 0.020 mmol, Intermediate 51) in THF (0.5 mL) and the mixture was stirred for 2 days at room temperature. TFA (1 mL) and water (0.5 mL) were added and the mixture was stirred overnight. The mixture was evaporated and dissolved in MeOH, filtered and purified by reversed phase preparative HPLC using ACE Prep UV C8 150×30 mm, flow 38 mL/min, gradient time 8.5 min using the eluent system: water/0.1% TFA and CH3CN (31-62% MeCN), fractions collected based on UV-signal (254 nm). The purest fractions were pooled and the acetonitrile was evaporated. Yield: 2.7 mg (22%). Colorless oil. MS (electronspray; [M+H]+) m/z 386.4.

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe mixture was evaporated
  3. dissolutiondissolved in MeOH
  4. filtrationfiltered
  5. custompurified by reversed phase preparative HPLC
  6. custom38 mL/min, gradient time 8.5 min
  7. customwater/0.1% TFA and CH3CN (31-62% MeCN), fractions collected
  8. customthe acetonitrile was evaporated

Sources & evidence

ORD record
ord-1da7b76a9c7e4ae8a709bf1e982d0c3b
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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