4-(Bromoacetyl)phenyl benzoate → HCID 131720296, compound

HRID 2293413Notes

Reaction equation

HRID 2293413 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[CH2:9]([NH:16][C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:25]([O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40](=[O:43])[CH2:41]Br)=[CH:36][CH:35]=1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:25]([O:33][C:34]1[CH:35]=[CH:36][C:37]([C:40](=[O:43])[CH2:41][N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([N:16]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])=[O:5])=[CH:38][CH:39]=1)(=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 2203054-(Bromoacetyl)phenyl benzoateHCID 86751513HCID 86751513, compound

Product 1

HCID 131720296HCID 131720296, compoundYield 48.8%

Procedure

Using the procedure described in Example 5, treatment of L-proline-L-isoleucine benzylamide (200 mg, 0.63 mmol) with 4'-benzoyloxy-2-bromoacetophenone (302 mg, 0.95 mmol, 1.5 eq) provided 171 mg of L-isoleucine, N-[1-(2-(4-benzoyloxyphenyl)-2-oxoethyl)-L-prolyl] benzylamide as a foam.

Sources & evidence

ORD record
ord-9932f66ebb2546d29e98d523c4198b01
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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