Tert-butoxycarbonylalanine → HCID 70205253, compound

HRID 583206Notes

Reaction equation

HRID 583206 reaction equation
[CH:1]1[CH:6]=[C:5]2[N:7]=NN(O)[C:4]2=[CH:3][CH:2]=1.O.[C:12]([O:16][C:17]([NH:19][C@H:20]([C:22]([OH:24])=O)[CH3:21])=[O:18])([CH3:15])([CH3:14])[CH3:13].[C:25]1([C@H:31]2[CH2:35][N:34]([S:36]([C:39]3[CH:40]=[C:41]4[C:45](=[CH:46][CH:47]=3)[N:44]([C:48](=[O:56])C3C=CC(N)=CC=3)[CH2:43][CH2:42]4)(=[O:38])=[O:37])[C:33](=[O:57])[NH:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C1C=CN=CC=1.O1CCCC1>[C:25]1([C@H:31]2[CH2:35][N:34]([S:36]([C:39]3[CH:40]=[C:41]4[C:45](=[CH:46][CH:47]=3)[N:44]([C:48](=[O:56])[C:4]3[CH:3]=[CH:2][C:1]([C:22](=[O:24])[CH:20]([NH:19][C:17]([O:16][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:18])[CH3:21])=[CH:6][C:5]=3[NH2:7])[CH2:43][CH2:42]4)(=[O:38])=[O:37])[C:33](=[O:57])[NH:32]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 85082Tert-butoxycarbonylalanineHCID 27960291-Hydroxybenzotriazole hydrateHCID 9870546DW-2282 free base

Product 1

HCID 70205253HCID 70205253, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,3-dicyclohexylcarboimide (483 mg, 2.15 mmol) and 1-hydroxybenzotriazolehydrate (291 mg 2.15 mmol) in 10 m of tetrahydrofuran were added N-(t-butoxycarbonyl)-L-alanine (352 mg, 1.86 mmol) and 4-dimethylaminopyridine (50 mg, 0.41 mmol) in order. The reaction mixture was stirred at room temperature for 5 min. Then, (S)-(+)-4-phenyl-1-[N-(4-aminobenzoyl)-indoline-5 -sulfonyl]-4,5-dihydro-2-imidazolone (200 mg, 0.41 mmol) prepared in Example 65 was added thereto and the whole mixture was stirred at room temperature for 24 hours. After stirring, the reaction mixture was filtered. The filtrate was diluted with ethylacetate, washed with brine, dried over anhydrous magnesium sulfate, and then concentrated. The crude product thus obtained was purified by silica gel column chromatography (eluent: ethylacetate/hexane=2/1, v/v) to provide 260 mg (Yield: 96%) of (S)-(+)-4-phenyl-1-[N-{4-(2-t-butoxycarbonylaminopropanoyl)-aminobenzoyl}indoline-5-sulfonyl]-4,5-dihydro-2-imidazolone.

Workup

  1. stirringthe whole mixture was stirred at room temperature for 24 hours
  2. stirringAfter stirring
  3. filtrationthe reaction mixture was filtered
  4. additionThe filtrate was diluted with ethylacetate
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe crude product thus obtained
  9. customwas purified by silica gel column chromatography (eluent: ethylacetate/hexane=2/1, v/v)

Sources & evidence

ORD record
ord-ba444cb41e524fc3acdc1ace584827e4
Source dataset
uspto-grants-1999_07
Patent number
US05929103

Reaction notes

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