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Lithium Hydroxide → HCID 22730282, compound

HRID 2085800
Notes
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Reaction equation

HRID 2085800 reaction equation
CO[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH:16]=2)=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-].[N+:26]([C:29]1[CH:30]=[C:31]([S:45]([NH2:48])(=[O:47])=[O:46])[CH:32]=[CH:33][C:34]=1[NH:35][CH2:36][CH2:37][S:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([O-:28])=[O:27].CCN=C=NCCCN(C)C>C1COCC1.CO.CN(C1C=CN=CC=1)C.ClC(Cl)C.C(OCC)(=O)C.O>[N+:26]([C:29]1[CH:30]=[C:31]([S:45]([NH:48][C:3]([C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH:16]=3)=[CH:7][CH:6]=2)=[O:4])(=[O:46])=[O:47])[CH:32]=[CH:33][C:34]=1[NH:35][CH2:36][CH2:37][S:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([O-:28])=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

11

Reactant 4

HCID 3939Lithium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 8461424HCID 8461424, compoundHCID 22730763HCID 22730763, compound

Product 1

HCID 22730282HCID 22730282, compound

Reagents, catalysts & solvents 6

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 887MethanolSolvent
HCID 962WaterSolvent
HCID 63651,1-DichloroethaneSolvent
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 455B (1 g, 3.1 mmol) and LiOH (0.264 mg 6.2 mmol) in THF (15 mL), methanol (2.5 mL), and water (1.5 mL) was heated to 50° C. for 3 hours and concentrated. The concentrate was dissolved in DMF (10 mL) and treated with a mixture of Example 77B (1.059 g, 3 mmol), EDCI (1.146 g, 6 mmol), and DMAP (1.830, 15 mmol) in dichloroethane (10 mL), stirred for 16 hours, diluted with ethyl acetate (250 mL0, washed sequentially with 1N HCl (50 mL, water (100 mL) and brine (100 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5% methanol/dichloromethane to provide the desired product. MS (ESI(−)) m/e 637 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ8.78 (br t, 1H), 8.60 (d, 1H), 7.92 (dd, 1H), 7.85 (d, 2H), 7.55 (d, 2H), 7.40-7.15 (m, 6H), 6.35 (m, 1H), 4.21 (d, 2H), 3.65 (m, 2H), 3.52 (t, 2H), 3.25 (m, 4H), 1.45 (s, 9H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in DMF (10 mL)
  3. washwashed sequentially with 1N HCl (50 mL, water (100 mL) and brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-ec1bea58b6484f58bc37baff3055fbb5
Source dataset
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06720338B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes