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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 1013543
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HRID 1013543 반응식
[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
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반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a92d7ac8ee2245f7a7624748dec090af
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07981874B2

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