HCID 66716692, compound → HCID 67284088, compound

HRID 1184442Notes

Reaction equation

HRID 1184442 reaction equation
[CH3:1][CH:2]1[O:7][C:6]2[CH:8]=[CH:9][C:10]([CH2:12][CH2:13][C:14](O)=[O:15])=[CH:11][C:5]=2[NH:4][C:3]1=[O:17]>C1COCC1>[OH:15][CH2:14][CH2:13][CH2:12][C:10]1[CH:9]=[CH:8][C:6]2[O:7][CH:2]([CH3:1])[C:3](=[O:17])[NH:4][C:5]=2[CH:11]=1

Participants

3

Reactant 1

HCID 66716692HCID 66716692, compound

Product 1

HCID 67284088HCID 67284088, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 50 mL round bottom flask under nitrogen was added 185 (161 mg, 0.68 mmol) and THF (1 mL). The mixture was stirred magnetically at 0° C. and then BH3 in THF (1 M, 2.25 mL, 2.25 mmol) was added slowly dropwise. After 1 h, the reaction was quenched with HCl in MeOH (2 M, 1.4 mL). The reaction was concentrated in vacuo and the residue was purified by preparative HPLC-MS using a 15-40% MeCN in water gradient. The appropriate fractions were collected and concentrated in vacuo to give the title compound as a white solid (39 mg, 26% yield): 1H NMR (400 MHz, DMSO-d6) δ ppm 1.39 (d, J=6.82 Hz, 3H) 1.61-1.69 (m, 2H) 3.37-3.42 (m, 2H) 4.47 (br. s., 1H) 4.56-4.63 (m, 1H) 6.70 (d, J=2.02 Hz, 1H) 6.71-6.76 (m, 1H) 6.84 (d, J=8.08 Hz, 1H) 10.58 (s, 1H). ESI-MS: m/z 222.2 (M+H)+.

Workup

  1. customthe reaction was quenched with HCl in MeOH (2 M, 1.4 mL)
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe residue was purified by preparative HPLC-MS
  4. customThe appropriate fractions were collected
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b80227dc726f420d8456608dfa9f4399
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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