Hydrochloric Acid → HCID 70381215, compound

HRID 1762955Notes

Reaction equation

HRID 1762955 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([C:15](=[O:29])[CH2:16][N:17]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:11]=[CH:10][C:9]=2[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:5])C.O1CCCC1.[OH-].[Na+].[ClH:45]>CO>[ClH:45].[CH2:31]([O:30][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:29])[CH2:16][N:17]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:18]([CH3:21])([CH3:20])[CH3:19])=[C:13]2[C:8]=1[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]2)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 13243446HCID 13243446, compound

Product 1

HCID 70381215HCID 70381215, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10 g of 7-benzyloxy-4-(N-benzyl-N-tert-butylaminoacetyl)-2-indolecarboxylic acid ethyl ester is combined with 300 ml of tetrahydrofuran, 300 ml of methanol, and 100 ml of 2N sodium hydroxide solution and stirred for 4 hours at room temperature. Then 120 ml of 2N hydrochloric acid is added and the mixture concentrated until the onset of crystallization. The crystallized product is vacuum-filtered and the mother liquor once more concentrated. The resultant secondary crystallization product is combined with the first-obtained crystallized product, dried, and recrystallized from methanol/ethyl acetate, thus obtaining 8.8 g of 7-benzyloxy-4-(N-benzyl-N-tert-butylaminoacetyl)indole-2-carboxylic acid hydrochloride, decomposition point 158° C.

Workup

  1. concentrationthe mixture concentrated until the onset of crystallization
  2. filtrationThe crystallized product is vacuum-filtered
  3. concentrationthe mother liquor once more concentrated
  4. customcrystallized product
  5. customdried
  6. customrecrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-70c6e6fcf02f4de5ad9ef26d2789313e
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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