Water → HCID 58664764, compound

HRID 2222877Notes

Reaction equation

HRID 2222877 reaction equation
[C:1]([O-:4])([OH:3])=O.[Na+].S(C1C=[CH:15][C:13]([CH3:14])=[CH:12]C=1)(O)(=O)=O.[CH2:17]([O:19][C:20](=[O:34])[C@H:21]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([N+:31]([O-:33])=[O:32])[CH:25]=1)[NH2:22])[CH3:18].O.[CH2:36]1COCC1>>[CH3:12][C:13]([CH3:15])([CH3:36])[CH2:14][O:3][C:1]([NH:22][C@@H:21]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([N+:31]([O-:33])=[O:32])[CH:25]=1)[C:20]([O:19][CH2:17][CH3:18])=[O:34])=[O:4]

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 516892Sodium BicarbonateHCID 87235623HCID 87235623, compound

Product 1

HCID 58664764HCID 58664764, compound

Procedure

81.3 g of NaHCO3 are added in small portions to a solution of 206.4 g of (S)-3-nitrotyrosine ethyl ester tosylate in 750 of water and 250 ml of THF. A solution of 60 ml of 2,2-dimethylpropyl chloroformate (neopentyl chloroformate) in 250 ml of THF is then slowly added dropwise, and the mixture is stirred at room temperature for a further 2 hours. After removal of the solvent, the mixture is subjected to conventional work-up, giving 12.

Workup

  1. customAfter removal of the solvent

Sources & evidence

ORD record
ord-a0fc518e9fdd4f8f88bfc7346b15dd4c
Source dataset
uspto-grants-2008_05
Patent number
US07371854B2

Reaction notes

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