Water → HCID 66716120, compound

HRID 2173759Notes

Reaction equation

HRID 2173759 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][N:10]([S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N+:39]([O-:41])=[O:40])(=[O:32])=[O:31])[CH2:11][CH2:12][O:13][C:14]1[CH:19]=[C:18]([C:20](OCC)=[O:21])[N:17]=[C:16]([C:25](OCC)=[O:26])[CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[Cl-].[Cl-].[Ca+2].O>C(O)C>[OH:26][CH2:25][C:16]1[CH:15]=[C:14]([O:13][CH2:12][CH2:11][N:10]([S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[N+:39]([O-:41])=[O:40])(=[O:31])=[O:32])[CH2:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:19]=[C:18]([CH2:20][OH:21])[N:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 66714132HCID 66714132, compound

Product 1

HCID 66716120HCID 66716120, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.8 g of diethyl 4-{2-[(2-tert-butoxycarbonyl-ethyl)-(2-nitro-benzenesulfonyl)-amino]-ethoxy}-pyridine-2,6-dicarboxylate in 80 mL of ethanol were successively added 152 mg of sodium borohydride and 447 mg of CaCl2. The mixture was stirred at room temperature and 20 ml of water were then added at the end of the reaction. The ethanol was removed under reduced pressure, 100 ml of water were added to the residue obtained and the aqueous phase was extracted 3× with EtOAc. The organic phases were combined, washed with saturated NaCl solution, dried over MgSO4 and concentrated under reduced pressure. 670 mg of tert-butyl 3-[[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-(2-nitro-benzenesulfonyl)-amino]-propanoate were obtained. LC/MS (C): tr=3 min; [M+H]+: m/z 512.

Workup

  1. customThe ethanol was removed under reduced pressure, 100 ml of water
  2. additionwere added to the residue
  3. customobtained
  4. extractionthe aqueous phase was extracted 3× with EtOAc
  5. washwashed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc9c5bbcc845410aa63ebc50e71d4905
Source dataset
uspto-grants-2015_06
Patent number
US09056914B2

Reaction notes

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