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(4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide → (-)-(cis)-7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine (4S)-2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide

HRID 1668358
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HRID 1668358 반응식
[Br:1][C:2]1[C:22]([F:23])=[CH:21][C:5]2[O:6][C:7]3[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:8]=3[C@H:9]3[C@H:14]([NH2:15])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1.[CH3:24][C:25]1([CH3:39])[C@@H:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:30][P:28]([OH:38])(=[O:29])[O:27][CH2:26]1>C(Cl)Cl.CC(O)C.C(O)C>[OH:38][P:28]1(=[O:29])[O:30][C@@H:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:25]([CH3:24])([CH3:39])[CH2:26][O:27]1.[Br:1][C:2]1[C:22]([F:23])=[CH:21][C:5]2[O:6][C:7]3[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:8]=3[C@H:9]3[C@H:14]([NH2:15])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1
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참가 물질

6

반응물 2

HCID 9829482(4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxideHCID 67359100(-)-(cis)-7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine

생성물 1

HCID 67360179(-)-(cis)-7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine (4S)-2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide수율 39.9%

시약·촉매·용매 3

HCID 702
Ethanol
용매
2회
HCID 3776Isopropanol용매2회
HCID 6344Dichloromethane용매2회

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온도
40 °C

실험 절차

To a solution of (±)-(cis)-7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine (12.06 g, 31.65 mmol) in 120 mL of CH2Cl2, 25 mL of 2-propanol and 25 mL of ethanol at 40° C. was added a warm solution of (+)-phencyphos (3.84 g, 15.82 mmol) in 50 mL of CH2Cl2, 25 mL of 2-propanol and 25 mL of ethanol. The mixture was heated at 40° C., CH2Cl2 was carefully evaporated until a small amount of crystals was formed, and then the mixture was gradually cooled down to ambient temperature. The precipitate was filtered off and recrystallized to yield the title compound (3.94 g, 20%).

후처리

  1. customCH2Cl2 was carefully evaporated until a small amount of crystals
  2. customwas formed
  3. temperaturethe mixture was gradually cooled down to ambient temperature
  4. filtrationThe precipitate was filtered off
  5. customrecrystallized

출처 및 근거

ORD 기록
ord-64a465aed06e4e23a105ee6836ba091a
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07989442B2

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