Lithium Hydroxide → HCID 57611964, compound

HRID 1919882Notes

Reaction equation

HRID 1919882 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:23][C:24]2[CH:29]=[C:28]([C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[CH:27]=[CH:26][C:25]=2[NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:22])=[CH:17][CH:16]=1)[C:10]([O:12]CC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O.Cl>[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]1[CH:16]=[CH:17][C:18]([C:21]([NH:23][C:24]2[CH:29]=[C:28]([C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[CH:27]=[CH:26][C:25]=2[NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:22])=[CH:19][CH:20]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 57611905HCID 57611905, compound

Product 1

HCID 57611964HCID 57611964, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl [(tert-butoxycarbonyl)amino][4-({[2-[(tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]acetate (1.08 g, 1.813 mmol) and 1N lithium hydroxide (3.99 mL, 3.99 mmol) were stirred in THF (16 mL) at room temperature for 2 days. The reaction was diluted with water, 2 mL of 2N HCl was added and the products extracted into EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo to give the desired product as a pale yellow powder. 1H NMR (DMSO-d6, 600 MHz) δ 12.90 (br s, 1H), 9.90 (s, 1H), 8.72 (s, 1H), 7.94 (d, J=8.4 Hz, 2H), 7.81 (d, J=1.2 Hz, 1H), 7.72 (d, J=8.4 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 7.57 (d, J=8.4 Hz, 2H), 7.51 (m, 2H), 7.44 (d, J=3.6 Hz, 1H), 7.12 (dd, J=5.1 and 3.6 Hz, 1H), 5.23 (d, J=8.4 Hz, 1H), 1.45 (s, 9H), 1.39 (s, 9H). MS: cal'd 568 (MH+), exp 412, 456, 468 (MH+).

Workup

  1. additionwas added
  2. extractionthe products extracted into EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6eb2da190f9459dbefabc3805f53d52
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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