Water → Boc-D-cyclohexylglycine proline

HRID 482555Notes

Reaction equation

HRID 482555 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:16]([OH:18])=[O:17])[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])[CH3:3].C[O:20][C:21](=[O:27])[C@@H:22]1[CH2:26][CH2:25][CH2:24][NH:23]1.O.[Li+].[OH-].OS([O-])(=O)=O.[K+]>C1COCC1>[CH3:4][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:16]([OH:18])=[O:17])[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:1])[CH3:3].[NH:23]1[CH2:24][CH2:25][CH2:26][C@H:22]1[C:21]([OH:27])=[O:20]

Participants

6

Reactant 4

HCID 962Water2×HCID 3939Lithium HydroxideHCID 516920Potassium bisulfate2×HCID 131720805Boc-D-cyclohexylglycine proline methyl ester

Product 1

HCID 131720806Boc-D-cyclohexylglycine prolineYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

26-1 (9.20 g) was dissolved in 90 ml of THF, adding 50 ml of H2O, followed by 21 ml of 2.0N LiOH in portions over a period of 2 hr. The solution was let stir 20 hr and the reaction was worked up by addition of dil. KHSO4 to neutrality, evacuation of solvent under reduced pressure to give a thick paste to which was added 200 ml of H2O in portions with stirring, followed by dil. KHSO4 to acidity (pH<2). After stirring for 1 hr, the solid was isolated by filtration, washing with H2O twice, and drying in vacuo to give 6.45 g (72% yield overall) of intermediary Boc-D-cyclohexylglycine-proline. Evaporation of the filtrate to a volume of <100 ml afforded 26-2.

Workup

  1. customto give a thick paste to which
  2. stirringwith stirring
  3. stirringAfter stirring for 1 hr
  4. customthe solid was isolated by filtration
  5. washwashing with H2O twice
  6. customdrying in vacuo

Sources & evidence

ORD record
ord-35f5f3ad6b9a4f1d86eb0ae6adfcf9d7
Source dataset
uspto-grants-1998_08
Patent number
US05798377

Reaction notes

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