1-Hydroxybenzotriazole → HCID 15435300, compound

HRID 617647Notes

Reaction equation

HRID 617647 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20](O)=[O:21])[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][CH:30]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH:31]([OH:36])[C:32]([F:35])([F:34])[F:33].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:29][CH:30]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:31](=[O:36])[C:32]([F:33])([F:34])[F:35])=[O:21])[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 102491135-benzyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydropyrimidin-1-ylacetic acidHCID 145032493-Amino-1,1,1-trifluoro-4-phenylbutan-2-ol

Product 1

HCID 15435300HCID 15435300, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (5-benzyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)acetic acid (title compound in Reference Example 2, 8.57 g, 22.6 mmol) and 3-amino-1,1,1-trifluoro-4-phenyl-2-butanol (title compound in Reference Example 1, 5.91 g, 27.2 mmol) in DMF (75 mL) were added WSCI hydrochloride (5.20 g, 27.2 mmol) and HOBT (6.10 g, 45.1 mmol). The resulting mixture was stirred at room temperature for 16 h, poured into 0.5N hydrochloric acid (500 mL), and then extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained by concentration of the extract was separated and purified by silica gel column chromatography (chloroform-ethyl acetate, 83:17) to give 11.4 g (87%) of 2-(5-benzyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidyl)-N-(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)-acetamide as colorless crystals.

Sources & evidence

ORD record
ord-b72884d3497e4f6781d6c55879cc45a7
Source dataset
uspto-grants-1999_09
Patent number
US05948785

Reaction notes

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