Triethylamine → Isohexane ethyl acetate

HRID 600340Notes

Reaction equation

HRID 600340 reaction equation
C[CH2:2][CH2:3]P(O)(O)=O.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[C:21]([OH:23])=[O:22])=[O:14])([CH3:11])([CH3:10])[CH3:9].[NH2:24][C@@H:25]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([S:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:38])=[O:37])=[CH:32][CH:31]=1)[C:26]([NH2:28])=[O:27].C(N(CC)CC)C>CN(C=O)C.[Cl-].[Na+].O.O>[C:21]([O:23][CH2:2][CH3:3])(=[O:22])[CH3:16].[CH3:26][CH2:25][CH2:29][CH:30]([CH3:35])[CH3:31].[NH2:28][C:26](=[O:27])[C@@H:25]([NH:24][C:21]([C@@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20][N:15]1[C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:14])=[O:23])[CH2:29][C:30]1[CH:31]=[CH:32][C:33]([S:36]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)(=[O:37])=[O:38])=[CH:34][CH:35]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 204484Propylphosphonic acidHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 57999691HCID 57999691, compound

Product 2

HCID 21882781Isohexane ethyl acetateHCID 67269081(s)-Tert-butyl 2-((s)-1-amino-1-oxo-3-(4-(phenylsulfonyl)phenyl)propan-2-ylcarbamoyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

A 50% solution of 1-propylphosphonic acid cyclic anhydride in DMF (226 mg) was added to a stirred solution of (S)-(−)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (81 mg), (S)-2-amino-3-(4-(phenylsulfonyl)phenyl)propanamide (90 mg) and triethylamine (0.206 mL) in DMF (2 mL) at 0° C. The resulting solution was stirred at 0° C. for 30 min then warmed to room temperature and stirred for a further 30 min. Water (50 mL) and saturated brine (30 mL) were added and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with 1:1 water/saturated brine (2×50 mL), dried over magnesium sulfate and the filtrate was concentrated in vacuo to afford a dark oil contaminated with DMF. This was purified by flash silica chromatography, eluting with 1:2 then 2:1 ethyl acetate/isohexane, then ethyl acetate to give the subtitle compound (125 mg) as a brown oil.

Workup

  1. temperaturethen warmed to room temperature
  2. stirringstirred for a further 30 min
  3. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic phases were washed with 1:1 water/saturated brine (2×50 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationthe filtrate was concentrated in vacuo
  7. customto afford a dark oil
  8. customThis was purified by flash silica chromatography
  9. washeluting with 1:2

Sources & evidence

ORD record
ord-a0fda6e290b942aaae29d1404a9fc312
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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