Water → diethyl 1-[3-[(tert-butoxycarbonyl)amino]butan-2-yl]-1H-indole-2,6-dicarboxylate

HRID 1748257Notes

Reaction equation

HRID 1748257 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[CH3:22][CH:23]1[CH:27]([CH3:28])OS(=O)(=O)[N:24]1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].O>CN(C=O)C.CCOC(C)=O>[C:34]([O:33][C:31]([NH:24][CH:23]([CH3:22])[CH:27]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:28])=[O:32])([CH3:37])([CH3:36])[CH3:35]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2×HCID 86682386Tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

Product 1

HCID 67236196diethyl 1-[3-[(tert-butoxycarbonyl)amino]butan-2-yl]-1H-indole-2,6-dicarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 60% NaH dispersion in mineral oil (596 mg, 14.9 mmol) in DMF (14 mL) at 0° C. is added a solution of diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 3.9 g, 14.9 mmol) in DMF (14 mL). The mixture is stirred for 40 min, then a solution of tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (3.8 g, 14.9 mmol) in DMF (7 mL) is added. The reaction mixture is stirred for 30 min at 0° C. and then is warmed to room temperature and stirred for 65 h. Water is added and the mixture is stirred for 15 min before EtOAc (50 mL) is added. Then the organic layer is separated, washed with aqueous NH4Cl solution, water, and brine, dried (MgSO4) and concentrated to afford the crude title compound, which was used directly in the next reaction.

Workup

  1. stirringThe reaction mixture is stirred for 30 min at 0° C.
  2. stirringstirred for 65 h
  3. additionis added
  4. customThen the organic layer is separated
  5. washwashed with aqueous NH4Cl solution, water, and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-513ca76f89ec4799a9e8582d3e5e7995
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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