(Z)-(S)-2-(3-Benzyloxypropyl)-5-tert-butoxycarbonylamino-hex-2-enedioic acid 6-tert-butyl ester 1-ethyl ester → 1-tert-Butyl 6-ethyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-hydroxypropyl)hexanedioate

HRID 1473723Notes

Reaction equation

HRID 1473723 reaction equation
[CH2:1]([O:3][C:4](=[O:35])/[C:5](/[CH2:24][CH2:25][CH2:26][O:27]CC1C=CC=CC=1)=[CH:6]\[CH2:7][C@H:8]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH3:2].C(OC(=O)/C(/CCCOCC1C=CC=CC=1)=C/C[C@H](NC(OC(C)(C)C)=O)C(OC(C)(C)C)=O)C>CO.[Pd]>[C:20]([O:19][C:17]([NH:16][C@@H:8]([CH2:7][CH2:6][CH:5]([CH2:24][CH2:25][CH2:26][OH:27])[C:4]([O:3][CH2:1][CH3:2])=[O:35])[C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 86678436(Z)-(S)-2-(3-Benzyloxypropyl)-5-tert-butoxycarbonylamino-hex-2-enedioic acid 6-tert-butyl ester 1-ethyl esterHCID 86678437(E)-(S)-2-(3-Benzyloxypropyl)-5-tert-butoxycarbonylamino-hex-2-enedioic acid 6-tert-butyl ester 1-ethyl ester

Product 1

HCID 866784391-tert-Butyl 6-ethyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-hydroxypropyl)hexanedioate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (Z)—(S)-2-(3-Benzyloxypropyl)-5-tert-butoxycarbonylamino-hex-2-enedioic acid 6-tert-butyl ester 1-ethyl ester and (E)-(S)-2-(3-Benzyloxypropyl)-5-tert-butoxycarbonylamino-hex-2-enedioic acid 6-tert-butyl ester 1-ethyl ester (270 mg, 0.55 mmol) and palladium (30.0 mg, 10% on charcoal) in methanol (30 mL) were stirred for 6 h at r.t. under a hydrogen atmosphere. Then the mixture was filtered through Celite® and concentrated under reduced pressure. The crude product was purified by column chromatography (silica, hexane/ethyl acetate gradient).

Workup

  1. filtrationThen the mixture was filtered through Celite®
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by column chromatography (silica, hexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-204db8b2acca4a0d8fea6e6360db6eea
Source dataset
uspto-grants-2015_04
Patent number
US09017645B2

Reaction notes

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