HCID 131710167, compound → L-Serine, O-(1,1-dimethylethyl)-N-L-α-glutamyl-, bis(1,1-dimethylethyl) ester

HRID 1606828Notes

Reaction equation

HRID 1606828 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:12]([NH:14][C@H:15]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:16][O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]>[Pd]>[NH2:1][C@H:2]([C:12]([NH:14][C@H:15]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:16][O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10]

Participants

3

Reactant 1

HCID 131710167HCID 131710167, compound

Product 1

HCID 10916435L-Serine, O-(1,1-dimethylethyl)-N-L-α-glutamyl-, bis(1,1-dimethylethyl) esterYield 83.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2.5 g. of palladium-on-carbon are added to the solution of 17.2 g. (32 mmoles) of Z-30-31-OtBu in 350 ml. of methanol, and gaseous hydrogen is bubbled into the mixture for 1 hour. The catalyst is removed by filtration, the filtrate is evaporated to dryness under reduced pressure, the solid residue is mixed with petroleum ether, and the mixture is filtered. 10.97 g. (83.4 %) of H-Glu(OtBu)-Ser(tBu)-OtBu are obtained. M.p.: 78°-82° C, Rf11 = 0.4.

Workup

  1. customof methanol, and gaseous hydrogen is bubbled into the mixture for 1 hour
  2. customThe catalyst is removed by filtration
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. additionthe solid residue is mixed with petroleum ether
  5. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-055ca1749ad24418b3d46b93683aecd7
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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