HCID 67442709, compound → HCID 67442531, compound

HRID 1400802Notes

Reaction equation

HRID 1400802 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[S:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][C:26]=3[O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][CH:37]([CH:42]([C:48]([O:50]CC)=[O:49])[C:43]([O:45]CC)=[O:44])[C:38]([F:41])([F:40])[F:39])=[CH:32][C:31]=3[F:53])[CH:21]=2)=[N:18][CH:19]=1)[CH2:9][CH2:10][O:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO>[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[S:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][C:26]=3[O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][CH:37]([CH:42]([C:43]([OH:45])=[O:44])[C:48]([OH:50])=[O:49])[C:38]([F:41])([F:39])[F:40])=[CH:32][C:31]=3[F:53])[CH:21]=2)=[N:18][CH:19]=1)[CH2:9][CH2:10][O:11][CH3:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 67442709HCID 67442709, compound

Product 1

HCID 67442531HCID 67442531, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 16 (1.794 g, 2.346 mmol) in a mixture of EtOH/1N NaOH (25 mL/11.7 mL) was stirred at RT overnight. The reaction mixture was then concentrated, diluted with water and the pH was adjusted to 3-4 by addition of 1N HCl. The resulting suspension was stirred for 30 min, and the solid was collected by filtration, rinsed with water, air-dried and dried under high vacuum to afford the title compound 17 (1.217 g; mixed with the acid 18) as a pale yellow fluffy solid. MS (m/z): 665.5 and 709.5 (M+H).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted with water
  3. additionthe pH was adjusted to 3-4 by addition of 1N HCl
  4. stirringThe resulting suspension was stirred for 30 min
  5. filtrationthe solid was collected by filtration
  6. washrinsed with water
  7. customair-dried
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-6987ea3e66344252bbb236a9bcf7373a
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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