Water → HCID 69366184, compound

HRID 397323Notes

Reaction equation

HRID 397323 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:26])[NH:9][C@@H:10]([CH3:25])[CH2:11][C:12]1[C:20]2[CH:19]=[C:18]([OH:21])[CH:17]=[CH:16][C:15]=2[N:14]2[CH2:22][CH2:23][CH2:24][C:13]=12)([CH3:6])([CH3:5])[CH3:4].[CH3:27][O:28][C:29](=[O:32])[CH2:30]Br.O>CS(C)=O.C(OCC)(=O)C>[CH3:27][O:28][C:29](=[O:32])[CH2:30][O:21][C:18]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:22][CH2:23][CH2:24][C:13]3=[C:12]([CH2:11][C@@H:10]([NH:9][C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:26])[CH3:25])[C:20]=2[CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 69364305HCID 69364305, compound

Product 1

HCID 69366184HCID 69366184, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.42 g sodium hydride 55-65% in oil was added to a solution of 3.3 g (S)-[2-(6-hydroxy-2,3-dihydro-1H-3a-aza-cyclopenta[a]inden-8-yl)-1-methyl-ethyl]-carbamic acid tert-butyl ester in 30 mL dimethylsulfoxide and the mixture stirred at room temperature for 30 min. 1.68 g bromoacetic acid methyl ester was added to the resulting solution and the mixture stirred at room temperature for 2 h. The mixture was distributed between water and ethyl acetate. The phases separated and the organic phase was washed with water and brine, dried over magnesium sulfate and evaporated to dryness. The residue crystallised under hexane and was dried to constant weight to yield 3.61 g of (S)-[8-(2-tert-butoxycarbonylamino-propyl)-2,3-dihydro-1H-3a-aza-cyclopenta[a]inden-6-yloxy]-acetic acid methyl ester as off white crystals melting at 87-88° C.

Workup

  1. stirringthe mixture stirred at room temperature for 2 h
  2. customThe phases separated
  3. washthe organic phase was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue crystallised under hexane
  7. customwas dried to constant weight

Sources & evidence

ORD record
ord-179b7839532f4c1d96359418984a9368
Source dataset
uspto-grants-2003_08
Patent number
US06610685B2

Reaction notes

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