Hydrochloric Acid → HCID 86660583, compound

HRID 1499376Notes

Reaction equation

HRID 1499376 reaction equation
C(=[N:8][C:9]1([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:14][CH2:13][C:12](=[O:15])[NH:11][C:10]1=[O:16])C1C=CC=CC=1.[ClH:32]>C1COCC1>[ClH:32].[NH2:8][C:9]1([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:14][CH2:13][C:12](=[O:15])[NH:11][C:10]1=[O:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86660582HCID 86660582, compound

Product 1

HCID 86660583HCID 86660583, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3 (3.6 g, 8.54 mmol) in THF (21 mL) was added portionwise aqueous 4 M HCl at 0° C. The mixture was allowed to reach room temperature and stirred over 5 h. A white precipitated that formed during the reaction was filtered and washed with THF. Two recrystallizations afforded 4 (2.88 g, 91.2%) as a white solid. 1H NMR (400 MHz, DMSO) δ 11.30 (s, 1H), 8.62 (br s, 3H), 7.46-7.15 (m, 5H), 4.97 (m, 2H), 3.59 (m, 2H), 2.98 (m, 2H), 2.76 (m, 1H), 2.58 (m, 1H), 2.24-1.97 (m, 2H), 1.85 (m, 2H), 1.74 (m, 1H), 1.21 (m, 1H).

Workup

  1. customto reach room temperature
  2. customA white precipitated
  3. customthat formed during the reaction
  4. filtrationwas filtered
  5. washwashed with THF
  6. customTwo recrystallizations

Sources & evidence

ORD record
ord-76e78bab73234a7bb651105bc9f2fe47
Source dataset
uspto-grants-2015_12
Patent number
US09200263B2

Reaction notes

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