Benzylamine → (S)-4-Benzylcarbamoyl-2-tert-butoxycarbonylamino-butyric acid benzyl ester

HRID 1185519Notes

Reaction equation

HRID 1185519 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[C@@H:10]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:12][C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH2:44]([NH2:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C=O)C.C(Cl)CCl>[CH2:1]([O:8][C:9](=[O:24])[C@@H:10]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:12][C:13](=[O:15])[NH:51][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1537081-(Phenylmethyl) hydrogen N-((1,1-dimethylethoxy)carbonyl)-L-glutamate

Product 1

HCID 15674275(S)-4-Benzylcarbamoyl-2-tert-butoxycarbonylamino-butyric acid benzyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 10.00 g (S)-2-tert-butoxycarbonylamino-pentanedioic acid 1-benzyl ester in 80 ml DMF were added 5.85 g EDC, 4.67 g HOBt, 10.8 ml DIPEA and 3.2 ml benzylamine at 0° C. After stirring for 12 h the reaction mixture was concentrated, the residue was dissolved in dichloromethane and subsequently extracted with aqueous LiCl (4%), 0.1 M HCl and saturated aqueous NaHCO3. The crude product obtained after evaporation of the solvent was purified by flash chromatography on silica using ethyl acetate/heptane 1:1 as eluent. Yield: 11.2 g colorless amorphous solid.

Workup

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. extractionsubsequently extracted with aqueous LiCl (4%), 0.1 M HCl and saturated aqueous NaHCO3

Sources & evidence

ORD record
ord-343d25a682e54961a1c2534450b038e9
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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