Hydrogen chloride-ethyl acetate → HCID 178462157, compound

HRID 366091Notes

Reaction equation

HRID 366091 reaction equation
[C:1]([NH:11][C:12](=[N:38][C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])[NH:13][CH2:14][CH2:15][CH2:16][C@H:17]([C:26]([NH:28][C@@H:29]([C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1)[CH3:30])=[O:27])[NH:18]C(OC(C)(C)C)=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[ClH:49].CCOC(C)=O>CCOC(C)=O>[ClH:49].[C:39]([NH:38][C:12](=[N:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2])[NH:13][CH2:14][CH2:15][CH2:16][C@H:17]([C:26]([NH:28][C@@H:29]([C:31]1[CH:32]=[CH:33][C:34]([OH:37])=[CH:35][CH:36]=1)[CH3:30])=[O:27])[NH2:18])([O:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:40]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 178462146HCID 178462146, compound

Product 1

HCID 178462157HCID 178462157, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-Nω,Nω '-bis(Cbz)-N2 -(Boc)-(R)-N-[1-(4-hydroxyphenyl)-ethyl]arginine amide (11.2 g; 16.4 mmol, from step (b) above) in EtOAc (300 mL) was treated with HCl/EtOAc (300 mL) and stirred overnight at room temperature. The product precipitated as a white residue from which the solvents were decanted. To the residue was added methanol (100 mL) followed by diethyl ether (50 mL). This mixture was slurried and then concentrated at reduced pressure to afford the sub-title compound as a white crushable foam (10.2 g; 100%).

Workup

  1. customThe product precipitated as a white residue from which the solvents
  2. customwere decanted
  3. additionTo the residue was added methanol (100 mL)
  4. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-79c282f7f72a4545827393200740da09
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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