4-(Heptyloxy)benzoyl chloride → 4-(2-(((Benzyloxy)carbonyl)amino)-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate

HRID 1889154Notes

Reaction equation

HRID 1889154 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([O:28][CH3:29])[CH:22]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30]([O:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C(Cl)Cl>[CH2:30]([O:37][C:38]1[CH:39]=[CH:40][C:41]([C:42]([O:27][C:24]2[CH:25]=[CH:26][C:21]([CH2:20][CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])=[CH:22][C:23]=2[O:28][CH3:29])=[O:43])=[CH:45][CH:46]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

4

Reactant 2

HCID 27241824-(Heptyloxy)benzoyl chlorideHCID 58545693Tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-methoxyphenyl)propanoate

Product 1

HCID 585458034-(2-(((Benzyloxy)carbonyl)amino)-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared using General Procedure 3: To a stirred solution of tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-methoxyphenyl)propanoate INT-2 (4.7 g, 11.71 mmol) and TEA (3.05 mL, 21.07 mmol) in DCM (50 mL) at 0° C. was added 4-(heptyloxy)benzoyl chloride (2.95 mL, 12.29 mmol) dropwise. After warming to room temperature and stirring for 10 min, the mixture was quenched with saturated aqueous NaHCO3 (50 mL) and water (50 mL). The organic layer was dried over MgSO4 and concentrated. The product was purified by chromatography (EA/hexanes) to afford 5.46 g (75%) of 4-(2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate INT-3. LCMS-ESI (m/z) calculated for C36H45NO8: 619; found 564 [M+H-tBu]+, tR=3.22 min (Method 4).

Workup

  1. customPrepared
  2. customthe mixture was quenched with saturated aqueous NaHCO3 (50 mL) and water (50 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe product was purified by chromatography (EA/hexanes)

Sources & evidence

ORD record
ord-2421371175614b8c83d39c36f1287c3b
Source dataset
uspto-grants-2013_08
Patent number
US08501982B2

Reaction notes

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