Diisopropylethylamine → HCID 66892758, compound

HRID 1270836Notes

Reaction equation

HRID 1270836 reaction equation
[C:1]1([C:7]2[O:11][C:10]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]3)=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O:22][C:23]([NH:25][CH:26]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:33][CH:32]=1)[C:27](O)=[O:28])=[O:24])([CH3:21])([CH3:20])[CH3:19].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:18]([O:22][C:23](=[O:24])[NH:25][CH:26]([CH2:30][C:31]1[CH:32]=[CH:33][C:34]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:35][CH:36]=1)[C:27](=[O:28])[N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]1[C:10]1[O:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][N:9]=1)([CH3:20])([CH3:21])[CH3:19]

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 2733179PyBroP2×HCID 4293568HCID 4293568, compound2×HCID 22147672HCID 22147672, compound

Product 1

HCID 66892758HCID 66892758, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.20 g (0.88 mmol) of 2-(5-phenyl-oxazol-2-yl)-piperidine, 0.36 g (1.05 mmol) of 2-tert-Butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionic acid, 0.49 g (1.05 mmol) of PyBrop and 0.287 mL of diisopropylethylamine was added 1 ml of dimethylformamide. The resulting mixture was allowed to stir under argon at room temperature overnight. The following morning, LC analysis indicated that about 20% of starting material remained. An additional 0.09 g (0.26 mmol) of 2-tert-Butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionic acid, 0.12 g (0.26 mmol) of PyBrop and 0.072 ml (0.45 mmol) of diisopropylethylamine was added. After stirring for 3 hours, the mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, dried over magnesium sulfate and concentrated. The product was taken to the next step as is without further purification.

Workup

  1. stirringAfter stirring for 3 hours
  2. customthe mixture was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customas is without further purification

Sources & evidence

ORD record
ord-5c8fed6d6dbd4970a4643c2776bc767f
Source dataset
uspto-grants-2007_04
Patent number
US07202381B2

Reaction notes

Loading…