Triethylamine → HCID 67208964, compound

HRID 339482Notes

Reaction equation

HRID 339482 reaction equation
[NH2:1][C@@H:2]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:3]([NH:5][C@@H:6]([CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:7]([OH:17])[C:8]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9])=[O:4].[CH:31]1[CH:36]=[C:35]2[C:37]3[CH:44]=[CH:43][CH:42]=[C:41]([C:45](O)=[O:46])[C:38]=3[C:39](=[O:40])[C:34]2=[CH:33][CH:32]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[CH2:20]([O:19][CH2:18][CH:6]([NH:5][C:3](=[O:4])[C@H:2]([NH:1][C:45]([C:41]1[C:38]2[C:39](=[O:40])[C:34]3[C:35](=[CH:36][CH:31]=[CH:32][CH:33]=3)[C:37]=2[CH:44]=[CH:43][CH:42]=1)=[O:46])[CH2:27][CH:28]([CH3:29])[CH3:30])[CH:7]([OH:17])[C:8]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 740839-Oxo-9H-fluorenecarboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58336661HCID 58336661, compound

Product 1

HCID 67208964HCID 67208964, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-[(3S)-3-[(2S)-2-amino-4-methylpentanoyl]amino-4-(benzyloxy)-2-hydroxyl butanoyl]aminoacetate (500 mg, 1.2 mmole), 9-Fluorenone-1-Carboxylic acid (266 mg, 1.2 mmole), and HBTU (587 mg, 1.6 mmole) were dissolved in DMF (10 mL). Et3N (330 ul, 2.4 mmole) was added and stirring was continued overnight. DMF was removed under reduced pressure. The residue was diluted with EtOAc and washed with water. The organic layer was dried over MgSO4, filtered, and concentrated by rotary evaporation. Purification by chromatography (silica, EtOAc, Rf=0.3) afforded ethyl 2-(4-(benzyloxy)-2-hydroxy-3-[((2R)-4-methyl-2-[(9-oxo-9H-1-fluorenyl)carbonyl]aminopentanoyl)amino]butanoylamino)acetate as a white solid (641 mg, 85%).

Workup

  1. customDMF was removed under reduced pressure
  2. additionThe residue was diluted with EtOAc
  3. washwashed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customPurification by chromatography (silica, EtOAc, Rf=0.3)

Sources & evidence

ORD record
ord-97a3e9505a7240b09e8878868ead23b4
Source dataset
uspto-grants-2014_11
Patent number
US08895497B2

Reaction notes

Loading…