Sodium borohydride → HCID 19754001, compound

HRID 1354527Notes

Reaction equation

HRID 1354527 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][NH:5][C:6](=C=S)[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:9].[BH4-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3](=[O:19])[CH2:4][NH:5][CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH3:9]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 21106013HCID 21106013, compound

Product 1

HCID 19754001HCID 19754001, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a suspension of the N-[(N-Boc)(N-methyl)(1-thiocarbonyl)-2-aminoethyl]-glycine methyl ester (2.67 g, 0.0097 mol) and NiCl26H2O (18.39 g, 0.077 mol) in THF:MeOH 1:1 (100 ml) at −20° C., NaBH4 (8.78 g, 0.23 mol) was slowly added so that the temperature did not exceed 0° C. After addition of the NaBH4, the reaction was allowed to go to room temperature. The reaction mixture was filtered several times through celite and evaporated to dryness. The product was isolated by column chromatography on silica gel with CH2CL2/MeOH 90:10 eluent. The yield of the title compound was 60%.

Workup

  1. customdid not exceed 0° C
  2. customto go to room temperature
  3. filtrationThe reaction mixture was filtered several times through celite
  4. customevaporated to dryness
  5. customThe product was isolated by column chromatography on silica gel with CH2CL2/MeOH 90:10 eluent

Sources & evidence

ORD record
ord-15cd1d39347c4e0ca7eb68ee45023ae9
Source dataset
uspto-grants-2007_05
Patent number
US07223833B1

Reaction notes

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