4-Methoxyphenylacetyl chloride → 4-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)methyl)phenyl 4-(heptyloxy)benzoate

HRID 923531Notes

Reaction equation

HRID 923531 reaction equation
[CH2:1]([O:8][C:9]1[CH:42]=[CH:41][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:24](=[O:32])[C:25]3[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=3)=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:43][O:44][C:45]1[CH:50]=[CH:49][C:48]([CH2:51][C:52](Cl)=[O:53])=[CH:47][CH:46]=1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:42]=[CH:41][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:24](=[O:32])[C:25]3[CH:26]=[CH:27][C:28]([NH:31][C:52](=[O:53])[CH2:51][C:48]4[CH:49]=[CH:50][C:45]([O:44][CH3:43])=[CH:46][CH:47]=4)=[CH:29][CH:30]=3)=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 27346884-Methoxyphenylacetyl chloride2×HCID 892531254-((4-amino-N-(2-(tert-butoxy)-2-oxoethyl)benzamido)methyl)phenyl 4-(heptyloxy)benzoate

Product 1

HCID 892531624-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)methyl)phenyl 4-(heptyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared using General Procedure 7: To a stirring solution of 4-((4-amino-N-(2-(tert-butoxy)-2-oxoethyl)benzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-4 (70 mg, 0.12 mmol) in DCM (2 mL) was added TEA (0.042 mL, 0.31 mmol) and 2-(4-methoxyphenyl)acetyl chloride (0.85 mL, 0.171 mmol). Additional TEA (0.042 mL, 0.31 mmol) and 2-(4-methoxyphenyl)acetyl chloride (0.85 mL, 0.171 mmol) were added and the reaction stirred for 30 min to yield 4-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-5. The crude reaction mixture was concentrated to 1.0 mL volume and carried onto the next step without further purification. LCMS-ESI (m/z) calculated for C43H50N2O8: 722; no m/z observed, tR=3.24 min (Method 3).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7696eeeeb9a04d4a9825c3f609d843c0
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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