Triethylamine → HCID 68408428, compound

HRID 1523441Notes

Reaction equation

HRID 1523441 reaction equation
CS([O:5][CH:6]1[CH:11]([CH3:12])[CH2:10][C:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])=[CH:8][CH:7]1[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=O)=O.C(N(CC)CC)C.C[C:38]([O:41]C(OC(OC(C)(C)C)=O)=O)(C)C>N1C=CC=CC=1>[CH3:12][CH:11]1[CH:6]2[CH:7]([N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:38](=[O:41])[O:5]2)[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 722382272-(Tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate

Product 1

HCID 68408428HCID 68408428, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (+/−)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate (1.0 equiv.) in pyridine (0.2 M) in a microwave vessel was heated to 110° C. for 10 min. The orange solution was then concentrated to dryness and worked up by partitioning between ethyl acetate and water. The organic phase was dried with sodium sulfate, filtered and concentrated. The crude material was dissolved in DCM (0.2 M) and triethyl amine (1.8 equiv.) was added to the reaction, followed by Boc2O (1.2 eqiv.). After stirring at room temperature for 40 min, the reaction was concentrated in vacuo and purified via silica gel column chromatography eluting with ethyl acetate and hexanes (1:1) to give (+/−)-tert-butyl 7-methyl-5-(3-nitropyridin-4-yl)-2-oxo-3a,6,7,7a-tetrahydrobenzo[d]oxazole-3(2H)-carboxylate as a white foam in 66% yield. LC/MS=376.0 (M+H), Rt=0.87 min.

Workup

  1. concentrationThe orange solution was then concentrated to dryness
  2. customby partitioning between ethyl acetate and water
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe crude material was dissolved in DCM (0.2 M)
  7. concentrationthe reaction was concentrated in vacuo
  8. custompurified via silica gel column chromatography
  9. washeluting with ethyl acetate and hexanes (1:1)

Sources & evidence

ORD record
ord-b13e4a9cedb9472f87b513dd29989aa5
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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