Ethyl Salicylate → Ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate

HRID 1026879Notes

Reaction equation

HRID 1026879 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:13]([O:17][C:18]([NH:20][CH:21]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:22](O)=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].CCN=C=NCCCN(C)C.CN(C1C=CC=CN=1)C>C(Cl)Cl>[C:13]([O:17][C:18]([NH:20][CH:21]([CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:22]([O:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:23])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 8365Ethyl SalicylateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 2696982-{[(Tert-butoxy)carbonyl]amino}-3-phenylpropanoic acid

Product 1

HCID 67173975Ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoateYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-hydroxybenzoate (0.5 g, 3.0 mmol) in CH2Cl2 (8 mL) was added 2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (0.8 g, 3.0 mmol), EDCI (0.63 g, 3.3 mmol) and dimethylaminopyridine (0.037 g, 0.3 mmol). The reaction was stirred (RT, 3 h) and then partitioned between CH2Cl2 and brine. The aqueous layer was extracted with CH2Cl2 and the combined organic extracts were dried over MgSO4. The crude material was purified by silica chromatography (0-10% MeOH/CH2Cl2) to afford 1.2 g of ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate. Mass calculated for C235H77NO6=413.46. found: [M+Na]+=437.1.

Workup

  1. custompartitioned between CH2Cl2 and brine
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. customThe crude material was purified by silica chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2b6c8ccfc3c84118b4432e3554c161f6
Source dataset
uspto-grants-2014_05
Patent number
US08729293B2

Reaction notes

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