Citric Acid → (S)-2-(4-(heptyloxy)phenyl)-2-oxoethyl 4-(2-(4-(tert-butyl)benzamido)-3-methoxy-3-oxopropyl)benzoate

HRID 1622991Notes

Reaction equation

HRID 1622991 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:7][CH:6]=1)=[O:4].[C:19]([C:23]1[CH:46]=[CH:45][C:26]([C:27]([NH:29][C@H:30]([C:41]([O:43][CH3:44])=[O:42])[CH2:31][C:32]2[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=2)=[O:28])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(#N)C>[C:19]([C:23]1[CH:46]=[CH:45][C:26]([C:27]([NH:29][C@H:30]([C:41]([O:43][CH3:44])=[O:42])[CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][CH2:2][C:3]([C:5]3[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:7][CH:6]=3)=[O:4])=[O:37])=[CH:39][CH:40]=2)=[O:28])=[CH:25][CH:24]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 539091862-Bromo-1-(4-(heptyloxy)phenyl)ethanoneHCID 86689655(S)-4-(2-(4-(tert-butyl)benzamido)-3-methoxy-3-oxopropyl)benzoic acid

Product 1

HCID 86689660(S)-2-(4-(heptyloxy)phenyl)-2-oxoethyl 4-(2-(4-(tert-butyl)benzamido)-3-methoxy-3-oxopropyl)benzoateYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2-bromo-1-(4-(heptyloxy)phenyl)ethanone, INT-4 (166 mg, 0.45 mmol) in acetonitrile (1 mL) was added to a solution of (S)-4-(2-(4-(tert-butyl)benzamido)-3-methoxy-3-oxopropyl)benzoic acid INT-1 (190 mg, 0.50 mmol) and TEA (75.0 μl, 0.54 mmol) in acetonitrile (4 mL). The reaction mixture was stirred at RT for 18 h then poured onto 0.5 M citric acid (30 mL) and extracted with EA (3×25 mL). The combined organics were dried over MgSO4, filtered and concentrated. The residue was triturated with Et2O (10 mL) and the filtrate concentrated to afford 159 mg (49%) of (S)-2-(4-(heptyloxy)phenyl)-2-oxoethyl 4-(2-(4-(tert-butyl)benzamido)-3-methoxy-3-oxopropyl)benzoate as a white solid. LCMS-ESI (m/z) calculated for C37H45NO7: 615.8; found 616.0 [M+H]+, tR=2.76 min. (Method 4).

Workup

  1. extractionextracted with EA (3×25 mL)
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was triturated with Et2O (10 mL)
  6. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-8093e191bc3b4eab98deaba056ede045
Source dataset
uspto-grants-2014_07
Patent number
US08778923B2

Reaction notes

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