Triethylamine → HCID 14874727, compound

HRID 1721237Notes

Reaction equation

HRID 1721237 reaction equation
C(N(CC)CC)C.[C:8]1([CH:14]([O:21][C:22](=[O:40])[C@@H:23](NC(OC(C)(C)C)=O)[CH2:24]C2C=CC(O)=CC=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClCCl.C(O)C>[C:8]1([CH:14]([O:21][C:22](=[O:40])[CH2:23][CH3:24])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 14560579HCID 14560579, compound

Product 1

HCID 14874727HCID 14874727, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (4.0 g, 39 mmol) was added dropwise to a suspension of (S)-2-[[(1,1-dimethylethoxy)carbonyl]-amino] -3-(4-hydroxyphenyl)propanoic acid diphenylmethyl ester (17.0 g, 38 mmol) and N-phenyl-N-trifluorosulfonyl -1,1,1-trifluoromethyl sulfonamide (13.6 g, 38 mmol) in dichloromethane (170 mL) at 0° C. After 1 hour the reaction mixture was warmed to room temperature and washed with 1N sodium hydroxide (2×25 mL), saturated aqueous sodium bicarbonate (2×25 mL) and water (2×25 mL). The organic layer was dried (K2CO3), filtered and concentrated. Recrystallization of the solid from hexane gave (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[4-trifluoromethyl)sulfonyl]oxy]phenyl]propanoic acid diphenylmethyl ester (13.7 g, 24 mmol) in 62% yield, mp. 110°-112° C., [α]D -14.23° (0.12% in ethanol).

Workup

  1. washwashed with 1N sodium hydroxide (2×25 mL), saturated aqueous sodium bicarbonate (2×25 mL) and water (2×25 mL)
  2. dry with materialThe organic layer was dried (K2CO3)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customRecrystallization of the solid from hexane

Sources & evidence

ORD record
ord-ddef3d5c963449e5b77fbefd481da7da
Source dataset
uspto-grants-1996_04
Patent number
US05508437

Reaction notes

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