Stannane → HCID 57190507, compound

HRID 1263616Notes

Reaction equation

HRID 1263616 reaction equation
[SnH4].C(OC([N:8]1[CH2:12][C@@H:11]([S:13]C(OC(C)(C)C)=O)[CH2:10][C@H:9]1[CH2:21][NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32](=[O:43])[NH:33][C@H:34]([C:39]([O:41][CH3:42])=[O:40])[CH2:35][CH2:36][S:37][CH3:38])[CH:27]=1)(=[O:25])=[O:24])=O)C=C.COC(=O)C(NC(=O)C1C=CC=C(S(=O)(=O)NC[C@@H]2C[C@H](SC(OC(C)(C)C)=O)CN2)C=1)CCSC>O.C(Cl)Cl>[CH3:42][O:41][C:39](=[O:40])[C@@H:34]([NH:33][C:32](=[O:43])[C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([S:23](=[O:24])(=[O:25])[NH:22][CH2:21][C@@H:9]2[CH2:10][C@H:11]([SH:13])[CH2:12][NH:8]2)[CH:27]=1)[CH2:35][CH2:36][S:37][CH3:38]

Participants

6

Reactant 3

HCID 123161StannaneHCID 57070558HCID 57070558, compoundHCID 86758896HCID 86758896, 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, elutins 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, elutins with a gradient of 0-10% EtOAc/i-Hexane
  6. customto give the

Sources & evidence

ORD record
ord-e16e3fc7eda945ad9db542786b6cf356
Source dataset
uspto-grants-2003_04
Patent number
US06541491B1

Reaction notes

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