Ethanol → HCID 67996287, compound

HRID 1907804Notes

Reaction equation

HRID 1907804 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:4][C:3]=1[NH:17][C:18]([C:20]1[S:24][C:23]2[CH2:25][C:26]([CH3:30])([CH3:29])[C:27](=[O:28])[C:22]=2[CH:21]=1)=[O:19].C(O)C.[BH4-].[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:15])([CH3:16])[O:9]2)=[CH:4][C:3]=1[NH:17][C:18]([C:20]1[S:24][C:23]2[CH2:25][C:26]([CH3:30])([CH3:29])[CH:27]([OH:28])[C:22]=2[CH:21]=1)=[O:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 67427596HCID 67427596, compound

Product 1

HCID 67996287HCID 67996287, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 27 (800 mg, 1.86 mmol) and ethanol (5.0 mL). Sodium borohydride (69 mg, 11.82 mmol) was added in one portion. The mixture was stirred at room temperature for 1 h and then neutralized with acetic acid to pH 7. The reaction was concentrated under reduced pressure and triturated with ethyl acetate (10 mL) to give a quantitative yield of 28 as a white semi-solid: 1H NMR (500 MHz, CDCl3) δ 8.75 (d, 1H, J=8.5 Hz), 7.78 (s, 1H). 7.53 (m, 2H), 7.10 (m, 1H), 4.58 (s, 1H), 2.88 (d, 1H, J=16.0 Hz), 2.69 (d, 1H, J=16.0 Hz), 1.32 (s, 12H), 1.20 (d, 611, J=6.5 Hz); MS (APCI+) m/z 431.4 (M+H).

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customtriturated with ethyl acetate (10 mL)

Sources & evidence

ORD record
ord-e5750cdab7e34561819420f17a600d12
Source dataset
uspto-grants-2013_12
Patent number
US08598174B2

Reaction notes

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