HCID 71152541, compound → HCID 86727207, compound

HRID 2274316Notes

Reaction equation

HRID 2274316 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:14]2[NH:15][C:16](=[O:18])[O:17][C@H:13]2[CH2:12][C@H:11]([CH2:19][OH:20])[C@H:10]1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl>[CH2:1]([O:8][C@@H:9]1[C@H:14]2[NH:15][C:16](=[O:18])[O:17][C@H:13]2[CH2:12][C@H:11]([CH:19]=[O:20])[C@H:10]1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 71152541HCID 71152541, compound

Product 1

HCID 86727207HCID 86727207, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 2 (1.4 g, 3.6 mmol) in DCM (25 mL) was treated with DMP (3.1 g, 7.3 mmol) for 3 h at room temperature. The reaction mixture was quenched with saturated aqueous Na2S2O3 (10 mL) and extracted with DCM (4×20 mL). The combined organic layer was washed with saturated aqueous NaHCO3 (20 mL) and brine (10 mL), dried over anhydrous MgSO4, and concentrated in vacuo to give the crude aldehyde 3 (1.4 g, yellow oil), which was used in the next step without further purification. (ES, m/z): [M+H]+ 382.0; 1H NMR (300 MHz, CDCl3), δ: 9.74 (s, 1H), 7.28-7.46 (m, 10H), 4.54-4.85 (m, 5H), 3.85-3.90 (m, 1H), 3.69-3.74 (m, 1H), 3.60-3.65 (m, 1H), 2.94-2.96 (m, 1H), 2.19-2.27 (m, 1H), 1.94-2.00 (m, 1H).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous Na2S2O3 (10 mL)
  2. extractionextracted with DCM (4×20 mL)
  3. washThe combined organic layer was washed with saturated aqueous NaHCO3 (20 mL) and brine (10 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e723c3ab8362414b9369816d12b28a49
Source dataset
uspto-grants-2015_09
Patent number
US09126957B2

Reaction notes

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