Sodium Bicarbonate → HCID 178450926, compound

HRID 1486889Notes

Reaction equation

HRID 1486889 reaction equation
Cl.[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4].[C:15]([O:19][C:20](=[O:50])[CH2:21][C:22]1([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[O:26][N:25]=[C:24]([C:27]2[CH:32]=[C:31]([OH:33])[CH:30]=[C:29]([CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH:28]=2)[CH2:23]1)([CH3:18])([CH3:17])[CH3:16].C(=O)(O)[O-].[Na+]>O.C(#N)C.CN1C(=O)CCC1.N1C=CC=CC=1>[C:15]([O:19][C:20](=[O:50])[CH2:21][C:22]1([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[O:26][N:25]=[C:24]([C:27]2[CH:32]=[C:31]([O:33][C:10](=[O:11])[C:9]3[CH:8]=[CH:7][C:6]([NH:2][C:3]([NH2:5])=[NH:4])=[CH:14][CH:13]=3)[CH:30]=[C:29]([CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:41])([CH3:40])[CH3:42])=[O:37])[CH:28]=2)[CH2:23]1)([CH3:16])([CH3:17])[CH3:18]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 118292873tert-Butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(3-(3-tert-butoxy-3-oxopropyl)-5-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylateHCID 178479379HCID 178479379, compound4×

Product 1

HCID 178450926HCID 178450926, compoundYield 47.4%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

4-Carbamimidamidobenzoyl chloride hydrochloride (77 mg) was added to a mixture of tert-butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(3-(3-tert-butoxy-3-oxopropyl)-5-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (167 mg), pyridine (0.16 mL), and NMP (0.16 mL) at 50 C, and the obtained mixture was stirred at 50 C for 30 minutes. Further, 4-carbamimidamidobenzoyl chloride hydrochloride (77 mg) was added thereto, and the obtained mixture was stirred at 50 C for 3 hours. Pyridine (0.16 mL) and NMP (0.16 mL) were added thereto, then 4-carbamimidamidobenzoyl chloride hydrochloride (77 mg) was added, and then, the obtained mixture was stirred at 50 C for 30 minutes. Further, 4-carbamimidamidobenzoyl chloride hydrochloride (77 mg) was added thereto, and the obtained mixture was stirred overnight at 50 C. The reaction mixture was fractionated by HPLC (C18, mobile phase: water/acetonitrile (system containing 0.1% TFA)). To the obtained fraction, a saturated aqueous solution of sodium bicarbonate was added, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (104 mg).

Workup

  1. stirringthe obtained mixture was stirred at 50 C for 3 hours
  2. stirringthe obtained mixture was stirred at 50 C for 30 minutes
  3. stirringthe obtained mixture was stirred overnight at 50 C
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4b572701fa224a9196a3043cc00387a5
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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