Acetic Acid → HCID 11384253, compound

HRID 131652Notes

Reaction equation

HRID 131652 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=O)[CH2:7]2.[CH:14]([C:17]1[S:21][C:20]([NH:22][C:23](=[O:29])[C@@H:24]([NH2:28])[CH2:25][CH2:26][CH3:27])=[N:19][CH:18]=1)([CH3:16])[CH3:15].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl.CCOC(C)=O>[CH:14]([C:17]1[S:21][C:20]([NH:22][C:23](=[O:29])[C@@H:24]([NH:28][CH:6]2[CH2:5][CH2:4][C:3]3[C:8](=[CH:9][C:10]([F:12])=[CH:11][C:2]=3[F:1])[CH2:7]2)[CH2:25][CH2:26][CH3:27])=[N:19][CH:18]=1)([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 36357585,7-Difluoro-2-tetraloneHCID 5049666Sodium triacetoxyborohydrideHCID 866045872-(S)-amino-pentanoic acid (5-isopropyl-thiazol-2-yl)amide

Product 1

HCID 11384253HCID 11384253, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 5,7-difluoro-2-tetralone (0.3 mmol) was dissolved in 2.0 mL of anhydrous dichloromethane under N2 at rt. 2-(S)-Amino-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide (0.3 mmol) was then added to the reaction solution, followed by sodium triacetoxy borohydride (0.3 mmol) and acetic acid (0.3 mmol). The reaction was stirred at rt for 16 h. The crude solution was then diluted with 20 mL of EtOAc and washed with 20 mL of aqueous 1N NaOH solution and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude products were purified through flash chromatography to give 2-(S)-(5,7-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide. LC-MS (retention time, M+1): 2.2 min, 408 [M+1].

Workup

  1. washwashed with 20 mL of aqueous 1N NaOH solution and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude products were purified through flash chromatography

Sources & evidence

ORD record
ord-6d769896f0fa49af902a766b337162a4
Source dataset
uspto-grants-2008_06
Patent number
US07384968B2

Reaction notes

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