Diisopropylamine → HCID 57535352, compound

HRID 1455574Notes

Reaction equation

HRID 1455574 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[C@@H:5]([NH2:14])[CH2:6][C:7]([F:13])([F:12])[CH2:8][CH:9]([CH3:11])[CH3:10].C(NC(C)C)(C)C.[N:23]1([C:29](Cl)=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>ClCCl>[CH3:2][O:3][C:4](=[O:15])[C@@H:5]([NH:14][C:29]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:30])[CH2:6][C:7]([F:13])([F:12])[CH2:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 848104-Morpholinecarbonyl chlorideHCID 86607344HCID 86607344, compound

Product 1

HCID 57535352HCID 57535352, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of (S)-2-amino-4,4-difluoro-6-methyl-heptanoic acid methyl ester hydrochloride (238 mg, 0.97 mmol) and diisopropyl amine (2.42 mmol, 313 mg) in dry dichloromethane (5 mL) under N2 is added drop wise morpholine carbonyl chloride (1.45 mmol, 218 mg). The mixture is stirred at room temperature for 23 h, then diluted with dichloromethane (25 mL) and washed with dilute HCl (30 mL), and saturated NaHCO3 (30 mL). The organic layers are dried over magnesium sulfate and concentrated in vacuum. Purification over 12 g silica gel, eluting with EtOAc:Heptane (1:1, then 2:1) affords (S)-4,4-Difluoro-6-methyl-2-[(morpholine-4-carbonyl)-amino]-heptanoic acid methyl ester (206 mg, 66%).

Workup

  1. washwashed with dilute HCl (30 mL), and saturated NaHCO3 (30 mL)
  2. dry with materialThe organic layers are dried over magnesium sulfate
  3. concentrationconcentrated in vacuum
  4. customPurification over 12 g silica gel
  5. washeluting with EtOAc:Heptane (1:1

Sources & evidence

ORD record
ord-758b4e300f2b4e8585e88bea7388b7a0
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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