Hydrochloric Acid → HCID 67158147, compound

HRID 550210Notes

Reaction equation

HRID 550210 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([C:27](O)=[O:28])[CH:21]=[CH:20]3)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:30].Cl.[CH2:35]([O:37][C:38](=[O:42])[CH2:39][NH:40][CH3:41])[CH3:36].Cl>CN(C1C=CN=CC=1)C.O>[CH2:35]([O:37][C:38](=[O:42])[CH2:39][NH:40][CH2:41][C:27]([C:22]1[CH:21]=[CH:20][C:19]2[C:24](=[CH:25][CH:26]=[C:17]([C:12]([C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3](=[O:31])[C:2]([CH3:33])([CH3:32])[CH3:1])=[C:7]([CH3:30])[CH:8]=3)([CH2:13][CH3:14])[CH2:15][CH3:16])[CH:18]=2)[CH:23]=1)=[O:28])[CH3:36]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 11554132HCID 11554132, compound

Product 1

HCID 67158147HCID 67158147, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

Dissolve 6-{1-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}naphthalene-2-carboxylic acid (0.10 g, 0.222 mmol), sarcosine ethyl ester HCl (0.069 g, 0.45 mmol), DMAP (0.108 g, 0.89 mmol) and EEDC (0.086 g, 0.45 mmol) in CH2CL2 (2 mL). Stir the mixture at RT for 16 h. Dilute the reaction mixture with CH2CL2 and water. Acidify to pH 1 using 1N HCl. Separate and discard the aqueous layer. Wash the organic layer with brine, dry over Na2SO4, and filter. Concentrate the filtrate and purify by silica gel radial chromatography (25:75 EtOAc:hex to 50:50 EtoAc:hex) to give the title compound as a white solid (0.093 g, 78%). MS (ES) m/e 546 (M+1).

Workup

  1. customSeparate
  2. washWash the organic layer with brine
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. concentrationConcentrate the filtrate
  6. custompurify by silica gel radial chromatography (25:75 EtOAc:hex to 50:50 EtoAc:hex)

Sources & evidence

ORD record
ord-6a3dc8b685b84980bd8d3cfb756dccf0
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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