Water → HCID 89785008, compound

HRID 1056127Notes

Reaction equation

HRID 1056127 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:12]=[CH:11][NH:10][C:9]=1[C@H:13]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1.O>C1COCC1.CCOC(C)=O>[CH2:17]([O:16][CH2:15][CH2:14][C@H:13]([C:9]1[N:10]([S:44]([C:41]2[CH:42]=[CH:43][C:38]([CH3:48])=[CH:39][CH:40]=2)(=[O:46])=[O:45])[CH:11]=[CH:12][C:8]=1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 23676156Sodium t-butoxideHCID 118511939HCID 118511939, compound

Product 1

HCID 89785008HCID 89785008, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-tert-Butyl 2-(3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)propyl)-1H-pyrrole-3-carboxylate (724b, 4.31 g, 10.01 mmol) was dissolved in THF (40 mL) under nitrogen and cooled in an ice bath. Sodium tert-butoxide (1M in THF, 10.01 mL, 10.01 mmol) was added and the mixture stirred for 5 min. Toluene-4-sulfonyl chloride (1.91 g, 10.01 mmol) was added to the solution and the mixture was stirred at 0° C. for 30 min. Water (50 mL) and EtOAc (50 mL) were added to the reaction mixture and the organic layer was washed with brine and dried over MgSO4, filtered and concentrated affording crude (R)-tert-butyl-2-(1-amino-3-(benzyloxy)propyl)-1-tosyl-1H-pyrrole-3-carboxylate (724c) as an orange viscous oil. m/z (ESI, +ve) 607.2 (M+Na)+.

Workup

  1. temperaturecooled in an ice bath
  2. stirringthe mixture was stirred at 0° C. for 30 min
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a6ad4bc723fd43ab8a6a23ed76b4de6c
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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