Diisopropylethylamine → HCID 58981734, compound

HRID 1182290Notes

Reaction equation

HRID 1182290 reaction equation
[NH2:1][CH2:2][C@@H:3]([C@@H:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:7][CH2:8][CH3:9])[OH:4].NC[C@H]([C@@H](NC(=O)OC(C)(C)C)CCCC)O.C(N(CC)C(C)C)(C)C.[N:44]1([C:50](Cl)=[O:51])[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>ClCCl>[OH:4][C@H:3]([C@@H:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][NH:1][C:50]([N:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1)=[O:51]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 58981684HCID 58981684, compoundHCID 58981744HCID 58981744, compound

Product 1

HCID 58981734HCID 58981734, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 100 mg (0.41 mmol) of tert-butyl (1S)-1-[(1S)-2-amino-1-hydroxyethyl]pentylcarbamate & tert-butyl (1S)-1-[(1R)-2-amino-1-hydroxyethyl]pentylcarbamate and 0.070 mL (0.41 mmol) of N,N-diisopropylethylamine in 2 mL dichloromethane was added 0.050 mL (0.41 mmol) 4-morpholinecarbonyl chloride. The reaction mixture was stirred at room temperature for 18 h, diluted with dichloromethane, and washed with 1N hydrochloric acid and brine. After drying over anhydrous magnesium sulfate, the solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography eluting with ethyl acetate to afford 130 mg (89%) of tert-butyl (1S)-1-{(1S)-1-hydroxy-2-[(4-morpholinylcarbonyl)amino]ethyl}pentylcarbamate & tert-butyl (1S)-1-{(1R)-1-hydroxy-2-[(4-morpholinylcarbonyl)amino]ethyl}pentylcarbamate. 1H-NMR (300 MHz, DMSO-d6): δ 6.55–6.36 (m, 2H), 5.00–4.65 (m, 1H), 3.60-3.23 (m, 9H), 3.10–2.80 (m, 2H), 1.40–1.05 (m, 15 H), 0.87 (m, 1H); ES-LCMS m/z 382 (M+Na).

Workup

  1. washwashed with 1N hydrochloric acid and brine
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. concentrationthe solution was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-5127f763f13f422c8cc567d8a5be9eba
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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