Benzyl Alcohol → HCID 22894888, compound

HRID 322735Notes

Reaction equation

HRID 322735 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([OH:17])=O)[CH3:14])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[CH2:18]([O:25][C:26](=[O:29])[CH2:27][NH2:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(NCC(O)=O)(OC(C)(C)C)=O.C(O)C1C=CC=CC=1>CO.C(Cl)Cl>[CH2:18]([O:25][C:26](=[O:29])[CH2:27][NH:28][C:15](=[O:17])[C@H:13]([CH3:14])[NH:12][C:10](=[O:11])[CH2:9][C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 78288N-(tert-butoxycarbonyl)glycineHCID 409140Benzyl glycinateHCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid

Product 1

HCID 22894888HCID 22894888, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Following General Procedure A and using N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and glycine benzyl ester (prepared from N-BOC-glycine (Bachem) and benzyl alcohol (Aldrich) using General Procedure X, followed by removal of the BOC-group using General Procedure Y), the title compound was prepared as a solid (mp=167.5° C.). The reaction was monitored by tlc (Rf=0.35 in 2% MeOH/CH2Cl2) and the product was purified by flash chromotography using 2% MeOH/CH2Cl2 as the eluent.

Workup

  1. customfollowed by removal of the BOC-group
  2. customwas prepared as a solid (mp=167.5° C.)
  3. customthe product was purified by flash chromotography

Sources & evidence

ORD record
ord-7fd0072101304eb7a088c26a72db7094
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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