Benzyloxycarbonylglycine → HCID 86757303, compound

HRID 651795Notes

Reaction equation

HRID 651795 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:19]([NH:21][N:22]1[C:26](=[O:27])[C:25]2([CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[NH:24][C:23]1=[O:33])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:38]([O:45][C:46]([NH:48][CH2:49][C:50](O)=[O:51])=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[CH2:38]([O:45][C:46]([NH:48][CH2:49][C:50]([N:30]1[CH2:31][CH2:32][C:25]2([NH:24][C:23](=[O:33])[N:22]([NH:21][C:19](=[O:20])[C@@H:18]([C@@H:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:34][CH:35]([CH3:37])[CH3:36])[C:26]2=[O:27])[CH2:28][CH2:29]1)=[O:51])=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 14349BenzyloxycarbonylglycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70203736HCID 70203736, compound

Product 1

HCID 86757303HCID 86757303, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.257 g of 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methyl-N-[2,4-dioxo-1,3,8-triazaspiro[4.5]decan-3-yl]valeramide and 0.209 g of N-(benzyloxycarbonyl)glycine in 5 ml of dry dimethylformamide was stirred and cooled to ice temperature. The mixture was treated with 0.225 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and was then stirred at room temperature for 2 days. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The ethyl acetate layer was washed successively with water, 5% aqueous sodium bicarbonate solution, saturated sodium chloride solution and dried over anhydrous magnesium sulphate. The solvent was evaporated and the residue triturated with ether and there was obtained 0.261 g of N-[8-{N-(benzyloxycarbonyl)aminoacetyl]-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methyl-N-[2,4-dioxo-1,3,8-triazaspiro[4.5]decan-3-yl]valeramide in the form of a white solid.

Workup

  1. temperaturecooled to ice temperature
  2. stirringwas then stirred at room temperature for 2 days
  3. customThe solvent was evaporated
  4. customthe residue partitioned between water and ethyl acetate
  5. washThe ethyl acetate layer was washed successively with water, 5% aqueous sodium bicarbonate solution, saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customThe solvent was evaporated
  8. customthe residue triturated with ether

Sources & evidence

ORD record
ord-5eb260fc4f3348a8aedc3476a1ab4dfa
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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