2-Methyltetrahydrofuran → HCID 66673339, compound

HRID 869316Notes

Reaction equation

HRID 869316 reaction equation
[CH:1]1([CH2:7][CH:8]([C:16]([O:18][CH3:19])=[O:17])[CH2:9][C@@H:10](O)S([O-])(=O)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na+].CC1CCCO1.[OH-].[Na+].Cl.[NH2:30][C@H:31]1[C:40]([CH2:43][CH3:44])([CH2:41][CH3:42])[C:39]2[CH:38]=[C:37]([C:45]([NH2:47])=[O:46])[CH:36]=[CH:35][C:34]=2[CH2:33][C@@H:32]1[O:48][CH3:49].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[CH3:19][O:18][C:16](=[O:17])[C@@H:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:9][CH2:10][NH:30][C@@H:31]1[C@@H:32]([O:48][CH3:49])[CH2:33][C:34]2[C:39](=[CH:38][C:37]([C:45](=[O:46])[NH2:47])=[CH:36][CH:35]=2)[C:40]1([CH2:43][CH3:44])[CH2:41][CH3:42]

Participants

7

Reactant 5

HCID 73012-Methyltetrahydrofuran2×HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 66674010HCID 66674010, compoundHCID 86631184HCID 86631184, compound

Product 1

HCID 66673339HCID 66673339, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a slurry of sodium (S)-4-cyclohexyl-1-hydroxy-3-methoxycarbonyl-butane-1-sulfonate (25.8 g, 81.5 mmol) and 2-methyl-tetrahydro-furan (300 mL) was added 1.0 M NaOH in water (76.1 mL) and the reaction mixture was stirred for 20 min at RT. To the reaction mixture was added (6S,7S)-7-amino-8,8-diethyl-6-methoxy-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid amide hydrochloride (17.0 g, 54.3 mmol); the reaction mixture was stirred for 40 min at RT, sodium triacetoxyborohydride (46.1 g, 217 mmol) was added in 4 portions. The reaction mixture was stirred at RT overnight after the first two portions. Water (200 mL) and MeTHF (100 mL) were added; the phases were separated and the organic layer was washed with 1 M NaOH (2×200 mL), diluted brine (200 mL) dried with Na2SO4 and solvent was removed to yield crude title intermediate (22 g) as a glassy yellow solid.

Workup

  1. stirringthe reaction mixture was stirred for 40 min at RT
  2. stirringThe reaction mixture was stirred at RT overnight after the first two portions
  3. customthe phases were separated
  4. washthe organic layer was washed with 1 M NaOH (2×200 mL), diluted brine (200 mL)
  5. dry with materialdried with Na2SO4 and solvent
  6. customwas removed

Sources & evidence

ORD record
ord-0f1fbdaa879149e5bfba88eec47b7efc
Source dataset
uspto-grants-2015_03
Patent number
US08969367B2

Reaction notes

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