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Triethylamine → HCID 58386786, compound

HRID 69998
Notes
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Reaction equation

HRID 69998 reaction equation
[O:1]=[C:2]1[NH:20][C@@H:5]2[CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:8][CH2:9][C@@H:4]2[O:3]1.[O:21](C(OC(C)(C)C)=O)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=O.C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[O:1]=[C:2]1[N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:21])[C@@H:5]2[CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[CH2:8][CH2:9][C@@H:4]2[O:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 58386792HCID 58386792, compound

Product 1

HCID 58386786HCID 58386786, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of (3aR,7aS)-benzyl 2-oxohexahydrooxazolo[4,5-c]pyridine-5(6H)-carboxylate (1.0 equiv.) in dichloromethane (0.09 M) was added BOC2O (1.1 equiv.), triethylamine (1.1 equiv.), and a catalytic amount of DMAP. The reaction was stirred at room temperature for one hour at which point it was concentrated under vacuo and filtered through a plug of silica gel eluting with ethylacetate. The product was dried under vacuo to give a white solid in 75% yield. LCMS (m/z): 277.2 (MH+), LC Rt=3.43 min.

Workup

  1. concentrationwas concentrated under vacuo
  2. filtrationfiltered through a plug of silica gel eluting with ethylacetate
  3. customThe product was dried under vacuo
  4. customto give a white solid in 75% yield

Sources & evidence

ORD record
ord-07ff35552b0e418b9ef63dd278fa15a5
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822497B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes