Ammonium Chloride → 1,1-Dimethylethyl [2-({[4-(2-methyl-2-oxido-1,2-oxaphospholan-5-yl)phenyl]carbonyl}amino)-4-(2-thienyl)phenyl]carbamate

HRID 1013543Notes

Reaction equation

HRID 1013543 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([C:29](=O)[CH2:30][CH2:31][P:32]([CH3:37])(=[O:36])[O:33]CC)=[CH:25][CH:24]=1)=[O:22])=[O:7])([CH3:4])[CH3:3].[BH4-].[Na+].[NH4+].[Cl-]>C1COCC1>[CH3:37][P:32]1(=[O:36])[CH2:31][CH2:30][CH:29]([C:26]2[CH:25]=[CH:24][C:23]([C:21]([NH:20][C:10]3[CH:11]=[C:12]([C:15]4[S:16][CH:17]=[CH:18][CH:19]=4)[CH:13]=[CH:14][C:9]=3[NH:8][C:6](=[O:7])[O:5][C:2]([CH3:4])([CH3:1])[CH3:3])=[O:22])=[CH:28][CH:27]=2)[O:33]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 57925974Ethyl {3-[4-({[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]-3-oxopropyl}methylphosphinate

Product 1

HCID 579260081,1-Dimethylethyl [2-({[4-(2-methyl-2-oxido-1,2-oxaphospholan-5-yl)phenyl]carbonyl}amino)-4-(2-thienyl)phenyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl {3-[4-({[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]-3-oxopropyl}methylphosphinate (0.7 g, 1.258 mmol) was taken up in THF (6 mL) and sodium borohydride (0.052 g, 1.383 mmol) was added before stirring overnight. Saturated NH4Cl was added and the products extracted into EtOAc (×2). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. Purification of the residue by MPLC followed by HPLC gave 1,1-dimethylethyl [2-({[4-(2-methyl-2-oxido-1,2-oxaphospholan-5-yl)phenyl]carbonyl}amino)-4-(2-thienyl)phenyl]carbamate as a white solid. The title compound was obtained as a ˜1:1 mixture of diastereosiomers.

Workup

  1. extractionthe products extracted into EtOAc (×2)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by MPLC

Sources & evidence

ORD record
ord-a92d7ac8ee2245f7a7624748dec090af
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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