Triethylamine → HCID 67475266, compound

HRID 2038396Notes

Reaction equation

HRID 2038396 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[O:8])[CH2:3]1.[C:14]([N:21]1[CH2:24][CH2:23][C:22]1=O)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(O)(=O)C>[S:10]1[CH:11]=[CH:12][N:13]=[C:9]1[C:7]([N:4]1[CH2:5][CH2:6][C@H:2]([NH:1][CH:23]2[CH2:22][N:21]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:24]2)[CH2:3]1)=[O:8]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23179885tert-Butyl 2-oxoazetidine-1-carboxylateHCID 67287646HCID 67287646, compound

Product 1

HCID 67475266HCID 67475266, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

To a solution of compound 1d (diHCl salt, 2.7 g, 10 mmol) and N-Boc azetidinone 1e (2.4 g, 14 mmol) in 1,2-DCE (50 mL) was added slowly Et3N (20 mmol) followed by acetic acid (3.5 mL). To this mixture was added Na(OAc)3BH (3.39 g, 16 mmol). The reaction was stirred at room temperature for 5 h. To the reaction mixture was added aq. NaHCO3, and the resultant mixture was extracted with CH2Cl2. The organic layer was dried over Na2SO4 and concentrated. Purification by flash column chromatography (silica gel, 80% EtOAc/heptane) gave compound 1f (2.96 g). 1H NMR (300 MHz, CDCl3): δ 7.91 (m, 1H), 7.53 (m, 1H), 4.28 (m, 1H), 4.22-4.11 (m, 2.5H), 3.91 (m, 0.5H), 3.83 (m, 1H), 3.73-3.60 (m, 3.5H), 3.49 (m, 0.5H), 3.41 (m, 1H), 2.11 (m, 1H), 1.89-1.73 (m, 1H), 1.44 (s, 9H).

Workup

  1. extractionthe resultant mixture was extracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customPurification by flash column chromatography (silica gel, 80% EtOAc/heptane)

Sources & evidence

ORD record
ord-3c1d99bbdb594779808934db270cd674
Source dataset
uspto-grants-2013_11
Patent number
US08575363B2

Reaction notes

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