Trimethyl orthobeznoate → HCID 58432809, compound

HRID 1045513Notes

Reaction equation

HRID 1045513 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[NH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:15]([NH2:23])([C:20]([NH2:22])=[O:21])[CH2:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:27]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(OC)OC>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:24])[NH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:15]1([C:20](=[O:21])[NH:22][C:27]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[N:23]1)[CH2:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69720Trimethyl orthobeznoateHCID 58432805HCID 58432805, compound2×

Product 1

HCID 58432809HCID 58432809, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (±)-benzyl[2-amino-2-(aminocarbonyl)-2,3-dihydro-1H-inden-5-yl]carbamate (described in Intermediate 1, 35.0 mg, 0.108 mmol) and (trimethoxymethyl)benzene (0.022 mL, 0.129 mmol) in toluene (5 mL) was heated at reflux for 7.5 h. The reaction mixture was concentrated under reduced pressure. The crude product was dissolved in DMSO (1 mL) and purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The pure, product-containing fractions were combined and concentrated to give the title compound. MS: m/z=412 (M+1).

Workup

  1. temperatureat reflux for 7.5 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe crude product was dissolved in DMSO (1 mL)
  4. custompurified by HPLC
  5. washeluting with a gradient of H2O
  6. additionThe pure, product-containing fractions
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3aa08ed039a9467d9897737bae701499
Source dataset
uspto-grants-2013_10
Patent number
US08569291B2

Reaction notes

Loading…