Pivalic acid → HCID 70381699, compound

HRID 1762956Notes

Reaction equation

HRID 1762956 reaction equation
[ClH:1].[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:22](=[O:36])[CH2:23][N:24]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:25]([CH3:28])([CH3:27])[CH3:26])=[C:14]2[C:18]=1[NH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:37](N(CC)CC)C.[CH3:44][C:45]([CH3:50])([CH3:49])[C:46]([OH:48])=[O:47]>CN(C)C=O>[ClH:1].[CH3:44][C:45]([CH3:50])([CH3:49])[C:46]([O:48][CH2:37][O:20][C:19]([C:16]1[NH:17][C:18]2[C:14]([CH:15]=1)=[C:13]([C:22](=[O:36])[CH2:23][N:24]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:25]([CH3:28])([CH3:27])[CH3:26])[CH:12]=[CH:11][C:10]=2[O:9][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:21])=[O:47]

Participants

5

Reactant 3

HCID 6417Pivalic acidHCID 8471TriethylamineHCID 70381215HCID 70381215, compound

Product 1

HCID 70381699HCID 70381699, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.00 g of 7-benzyloxy-4-(N-benzyl-N-tert-butylaminoacetyl)-2-indolecarboxylic acid hydrochloride, 1.4 ml of triethylamine, and 1.12 ml of the chloromethyl ester of trimethylacetic acid are combined with 15 ml of absolute dimethylformamide and stirred for 16 hours at room temperature. Then the mixture is concentrated, the residue dissolved in ethyl acetate, extracted three times with water, the organic phase is dried and concentrated, and the residue is chromatographed over an aluminum oxide column (activity stage II; eluent: cyclohexane/ethyl acetate 4+1). The product is recrystallized from diisopropyl ether/ethereal hydrochloric acid, yielding 0.7 g of 7-benzyloxy-4-(N-benzyl-N-tert-butylaminoacetyl)-2-indolecarboxylic acid trimethylacetoxymethyl ester hydrochloride, decomposition point 184°-185° C.

Workup

  1. concentrationThen the mixture is concentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. extractionextracted three times with water
  4. customthe organic phase is dried
  5. concentrationconcentrated
  6. customthe residue is chromatographed over an aluminum oxide column (activity stage II; eluent: cyclohexane/ethyl acetate 4+1)
  7. customThe product is recrystallized from diisopropyl ether/ethereal hydrochloric acid

Sources & evidence

ORD record
ord-0efcf3edb8154deaaa1f0104912ae6d9
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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