N-(tert-butoxycarbonyl)glycine → Methyl 3'-[(2-[[(tert-butoxy)carbonyl]amino]acetylamino)]-[1,1'-biphenyl]-3-carboxylate

HRID 1069084Notes

Reaction equation

HRID 1069084 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[C:18]([O:22][C:23]([NH:25][CH2:26][C:27](O)=[O:28])=[O:24])([CH3:21])([CH3:20])[CH3:19].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:18]([O:22][C:23]([NH:25][CH2:26][C:27]([NH:17][C:13]1[CH:12]=[C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=2)[CH:16]=[CH:15][CH:14]=1)=[O:28])=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 1394215(1,1'-Biphenyl)-3-carboxylic acid, 3'-amino-, methyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 54044428Methyl 3'-[(2-[[(tert-butoxy)carbonyl]amino]acetylamino)]-[1,1'-biphenyl]-3-carboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3′-amino-[1,1′-biphenyl]-3-carboxylic methyl ester (1.14 g) and N-(tert-butoxycarbonyl)glycine (0.879 g) in methylene chloride (20 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.20 g). The mixture was stirred for 3 h at room temperature, then washed twice with 1 N aqueous HCl, twice with saturated aqueous sodium bicarbonate and once with brine. The mixture was dried over sodium sulfate, filtered and concentrated to give a foam. Purification by silica gel chromatography eluting with 7:3 hexane/ethyl acetate gave 1.6 g of the title compound as a colorless oil. Electrospray MS (positive ion): (M+Na) 407.0.

Workup

  1. washwashed twice with 1 N aqueous HCl, twice with saturated aqueous sodium bicarbonate and once with brine
  2. dry with materialThe mixture was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a foam
  6. customPurification by silica gel chromatography
  7. washeluting with 7:3 hexane/ethyl acetate

Sources & evidence

ORD record
ord-24bd7fd9e1b3463cb322ccb92566000c
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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