Hydrochloric Acid → HCID 71519598, compound

HRID 2176038Notes

Reaction equation

HRID 2176038 reaction equation
Cl.[CH:2]1([N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:49])[NH:18][C:19]3[S:20][C:21]4[CH2:48][CH2:47][CH2:46][CH2:45][C:22]=4[C:23]=3[C:24](=[O:44])[NH:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]4[CH:39]=[CH:38][C:37]([C:40]([O:42][CH3:43])=[O:41])=[CH:36][CH:35]=4)=[CH:28][CH:27]=3)[CH:12]=2)[CH2:6][C:7](O)=[O:8])[CH2:4][CH2:3]1.Cl.[CH3:51][NH:52][CH2:53][C:54]([O:56][CH3:57])=[O:55].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>O.C(N(CC)CC)C.ClCCl>[CH:2]1([N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:49])[NH:18][C:19]3[S:20][C:21]4[CH2:48][CH2:47][CH2:46][CH2:45][C:22]=4[C:23]=3[C:24](=[O:44])[NH:25][C:26]3[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][C:34]4[CH:39]=[CH:38][C:37]([C:40]([O:42][CH3:43])=[O:41])=[CH:36][CH:35]=4)=[CH:30][CH:31]=3)[CH:12]=2)[CH2:6][C:7]([N:52]([CH3:51])[CH2:53][C:54]([O:56][CH3:57])=[O:55])=[O:8])[CH2:3][CH2:4]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 90370240HCID 90370240, compound

Product 1

HCID 71519598HCID 71519598, compoundYield 46.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 306 mg of N-cyclopropyl-N-[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)benzyl]glycine hydrochloride and 5.0 mL of dichloromethane were added 0.182 mL of triethylamine, 91 mg of methyl N-methylglycinate hydrochloride, 125 mg of WSC.hydrochloride and 88 mg of HOBt, followed by stirring for 15 hours at room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography, thereby obtaining 152 mg of methyl N-cyclopropyl-N-[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)benzyl]glycyl-N-methylglycinate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2e3977c0c61b4f379fc57603cb8cc7b5
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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