proline dl-form → HCID 58392432, compound

HRID 561433Notes

Reaction equation

HRID 561433 reaction equation
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:4]=2[O:3]1.[CH3:14][C:15]1([CH3:23])[O:22][C:20](=[O:21])[CH2:19][C:17](=[O:18])[O:16]1.N1CCCC1C(O)=O.[CH3:32][S:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[C:39]2[C:43]=1[NH:42][CH:41]=[CH:40]2>C(#N)C>[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]([C:40]3[C:39]4[C:43](=[C:35]([CH2:34][S:33][CH3:32])[CH:36]=[CH:37][CH:38]=4)[NH:42][CH:41]=3)[CH:19]3[C:20](=[O:21])[O:22][C:15]([CH3:23])([CH3:14])[O:16][C:17]3=[O:18])=[CH:10][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 614proline dl-formHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27369732,2-Difluoro-5-formylbenzodioxoleHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 58392432HCID 58392432, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.57 g (8.46 mmol) of 2,2-difluoro-1,3-benzodioxole-5-carbaldehyde, 1.22 g (8.46 mmol) of Meldrum's acid and 0.05 g (0.42 mmol) of D,L-proline were added to a solution of 1.50 g (8.46 mmol) of the compound from Example 8A in 12 ml of acetonitrile. The reaction mixture was stirred at RT overnight. The precipitated solid was filtered off with suction, washed with acetonitrile and dried under high vacuum. 2.67 g (91% of theory) of the title compound were obtained.

Workup

  1. filtrationThe precipitated solid was filtered off with suction
  2. washwashed with acetonitrile
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-2f70f418e60b4aa09a46c4a69ce53fde
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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