Hydrochloric Acid → (S)-Benzyl 2-((tert-butoxycarbonyl)amino)-5-hydroxypentanoate

HRID 1970577Notes

Reaction equation

HRID 1970577 reaction equation
[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:2]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:3][CH2:4][C:5](=O)[OH:6].C(N1CCOCC1)C.ClC(OCC(C)C)=O.[BH4-].[Na+].Cl>C1COCC1.CO>[CH2:11]([O:10][C:8](=[O:9])[C@@H:2]([NH:1][C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:3][CH2:4][CH2:5][OH:6])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 1537081-(Phenylmethyl) hydrogen N-((1,1-dimethylethoxy)carbonyl)-L-glutamateHCID 4311764Sodium borohydride

Product 1

HCID 11056397(S)-Benzyl 2-((tert-butoxycarbonyl)amino)-5-hydroxypentanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7.0 g Boc-Glu-OBn in 100 ml THF were added dropwise under Argon at −10° C. 2.9 ml N-ethylmorpholine and 3.0 ml isobutyl chloroformate. The reaction mixture was stirred for 10 minutes before 2.4 g sodium borohydride were added. Methanol (400 ml) was added slowly over a period of 70 minutes at this temperature. It was stirred for additional 30 minutes at RT before being neutralized with 1 N HCl. The mixture was concentrated, dissolved in ethyl acetate and washed with 1 N HCl and brine. The crude product obtained after evaporation of the solvent was purified by flash chromatography on silica using an ethyl acetate/heptane gradient. Yield: 5.3 g.

Workup

  1. additionwere added
  2. concentrationThe mixture was concentrated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with 1 N HCl and brine

Sources & evidence

ORD record
ord-bf1b36392d7e4c478cfa3d506cefae00
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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