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Hydrochloric Acid → HCID 53707024, compound

HRID 1789813
Notes
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Reaction equation

HRID 1789813 reaction equation
ClC(OC)=O.[C:6]([O:10][C:11](=[O:32])[C:12]([CH2:17][C:18]1[CH:19]=[N:20][C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:22][CH:23]=1)([CH3:16])[C:13](O)=[O:14])([CH3:9])([CH3:8])[CH3:7].CCN(CC)CC.[BH4-].[Na+].Cl>C1COCC1.CCOC(C)=O>[C:6]([O:10][C:11](=[O:32])[C:12]([CH2:13][OH:14])([CH3:16])[CH2:17][C:18]1[CH:19]=[N:20][C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:22][CH:23]=1)([CH3:7])([CH3:9])[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 54536141HCID 54536141, compound

Product 1

HCID 53707024HCID 53707024, compoundYield 57%

Reagents, catalysts & solvents

2
HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Methyl chloroformate (75 μL, 0.92 mmol) was added dropwise to a solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-methyl-malonic acid mono-tert-butyl ester (348 mg, 0.915 mmol) and Et3N (123 μL, 0.92 mmol) in THF (6 mL). The reaction mixture was stirred for 20 min., filtered and added dropwise to a suspension of NaBH4 (39 mg, 1.04 mmol) in THF (6 mL) at 0° C. The reaction was stirred for 16 h at room temperature. 0.2 M HCl was added followed by EtOAc. The organic phase was washed with brine and dried. Concentration under reduced pressure followed by chromathography (toluene/EtOAc, 3:1→1:3) gave 3-(6tert-butoxycarbonylamino-pyridin-3-yl)-2-hydroxymethyl-2-methyl-propionic acid tert-butyl ester (190 mg, 57%).

Workup

  1. filtrationfiltered
  2. stirringThe reaction was stirred for 16 h at room temperature
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-33705ed7c39b4002b3186b0f5b799ade
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07071175B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes