Stannane → HCID 57190507, compound

HRID 1977362Notes

Reaction equation

HRID 1977362 reaction equation
[SnH4].[CH3:2][O:3][C:4](=[O:37])[C@@H:5]([NH:10][C:11](=[O:36])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18](=[O:35])(=[O:34])[NH:19][CH2:20][C@@H:21]2[CH2:25][C@H:24]([S:26]C(OC(C)(C)C)=O)[CH2:23][NH:22]2)[CH:13]=1)[CH2:6][CH2:7][S:8][CH3:9]>O.C(Cl)Cl>[CH3:2][O:3][C:4](=[O:37])[C@@H:5]([NH:10][C:11](=[O:36])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18](=[O:34])(=[O:35])[NH:19][CH2:20][C@@H:21]2[CH2:25][C@H:24]([SH:26])[CH2:23][NH:22]2)[CH:13]=1)[CH2:6][CH2:7][S:8][CH3:9]

Participants

5

Reactant 2

HCID 123161StannaneHCID 86756698HCID 86756698, compound

Product 1

HCID 57190507HCID 57190507, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Tri-nButyl tin hydride (565 mL, 2.1 mmol) was added to a stirred solution of (15(c)) (1.18 g, 1.8 mmol) and (PPh)3PdCl2 (13 mg, 0.018 mmol) in a mixture of water (0.5 mL) and CH2Cl2 (100 mL). The reaction mixture was left to stir for 10 minutes, dried over MgSO4, filtered and concentrated to a brown oil. This was then purified by flash chromatography on 9385 SiO2, eluting with a gradient of 0-10% EtOAc/i-Hexane to give the desired starting material 15(d) as a white foam: 751 mg (73%).

Workup

  1. waitThe reaction mixture was left
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to a brown oil
  5. customThis was then purified by flash chromatography on 9385 SiO2
  6. washeluting with a gradient of 0-10% EtOAc/i-Hexane
  7. customto give the

Sources & evidence

ORD record
ord-4f33ca19ebfe4603868a1fe5fffabdc4
Source dataset
uspto-grants-2001_05
Patent number
US06232338B1

Reaction notes

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