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Boc-L-Valine → {(S)-1-[4-fluoro-2-(pyridin-3-ylamino)phenylcarbamoyl]-2-methylpropyl}carbamic acid tert-butyl ester

HRID 242963
Notes
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Reaction equation

HRID 242963 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:5]([NH2:8])=[CH:6][CH:7]=1.[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH:28]([CH3:30])[CH3:29])[C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C1C=NC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:16]([O:20][C:21](=[O:22])[NH:23][C@H:24]([C:25](=[O:26])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH:28]([CH3:29])[CH3:30])([CH3:17])([CH3:19])[CH3:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 83693Boc-L-ValineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 584592164-Fluoro-N2-pyridin-3-ylbenzene-1,2-diamine

Product 1

HCID 68157790{(S)-1-[4-fluoro-2-(pyridin-3-ylamino)phenylcarbamoyl]-2-methylpropyl}carbamic acid tert-butyl esterYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-fluoro-N2-pyridin-3-ylbenzene-1,2-diamine (685 mg, 3.0 mmol) in DCM (18 mL) at 0° C. were added (S)-2-tertbutoxycarbonylamino-3-methylbutyric acid (720 mg, 3.3 mmol), HOAt (0.450 g, 3.3 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.63 g, 3.3 mmol) and the resulting mixture stirred at 0° C. for 2 h. The reaction mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic layer was dried (MgSO4), concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-60% EtOAc in cyclohexane) to afford {(S)-1-[4-fluoro-2-(pyridin-3-ylamino)phenylcarbamoyl]-2-methylpropyl}carbamic acid tert-butyl ester (790 mg). LCMS (Method J): RT 2.10 min [M+H]+ 403.3

Workup

  1. customThe reaction mixture was partitioned between DCM
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe resulting residue purified by column chromatography (Si—PCC, gradient 0-60% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-257efabc601b47aba875f59f32c3d02e
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08653089B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes