Triethylamine → (R)-N-(2-methylbenzyl)-3-{(2S,3S)-3-[N-(tert-butoxycarbonyl)-L-asparaginyl]amino-2-hydroxy-4-phenylbutanoyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

HRID 1596318Notes

Reaction equation

HRID 1596318 reaction equation
C1C=CC2N(O)N=NC=2C=1.[NH:11]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:12]([C:17](OC1C=CC([N+]([O-])=O)=CC=1)=[O:18])[CH2:13][C:14](=[O:16])[NH2:15].CCN(CC)CC.[CH3:43][C:44]1[CH:73]=[CH:72][CH:71]=[CH:70][C:45]=1[CH2:46][NH:47][C:48]([C@@H:50]1[C:54]([CH3:56])([CH3:55])[S:53][CH2:52][N:51]1[C:57](=[O:69])[C@@H:58]([OH:68])[C@@H:59]([NH2:67])[CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:49]>CN(C=O)C.C(OCC)(=O)C>[CH3:43][C:44]1[CH:73]=[CH:72][CH:71]=[CH:70][C:45]=1[CH2:46][NH:47][C:48]([C@@H:50]1[C:54]([CH3:56])([CH3:55])[S:53][CH2:52][N:51]1[C:57](=[O:69])[C@@H:58]([OH:68])[C@@H:59]([NH:67][C:17](=[O:18])[C@H:12]([CH2:13][C:14](=[O:16])[NH2:15])[NH:11][C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[CH2:60][C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)=[O:49]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 439663L-Asparagine, N2-[(1,1-dimethylethoxy)carbonyl]-, 4-nitrophenyl esterHCID 10813054(R)-N-(2-methylbenzyl)-3-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

Product 1

HCID 70249347(R)-N-(2-methylbenzyl)-3-{(2S,3S)-3-[N-(tert-butoxycarbonyl)-L-asparaginyl]amino-2-hydroxy-4-phenylbutanoyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxamideYield 91.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HOBt (0.41 g), Boc-Asn-ONp (1.27 g), and Et3N (0.92 ml) were added to a solution of H-Apns-Dmt-NHBzl(2-Me) (1.32 g) obtained in the step 2 of Example 3 in DMF (20 ml) and the mixture was stirred overnight. After the addition of ethyl acetate, the reaction mixture was washed with 3% NaHCO3, 1N HCl, and 5% NaCl and dried over MgSO4. After filtration and concentration, the residue was recrystallized from AcOEt/n-hexane to obtain the title compound (1.79 g).

Workup

  1. washthe reaction mixture was washed with 3% NaHCO3, 1N HCl, and 5% NaCl
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration and concentration
  4. customthe residue was recrystallized from AcOEt/n-hexane

Sources & evidence

ORD record
ord-2c90bc545fa348ac9014a48a485b47e6
Source dataset
uspto-grants-2001_09
Patent number
US06291432B1

Reaction notes

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