Sodium Carbonate → (S)-tert-Butyl 4-(1-amino-3-(4-(3-(2-methoxyethyl)-2-oxo-2,3-dihydrobenzo[d]thiazol-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216926노트

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HRID 216926 반응식
[NH2:1][C:2](=[O:29])[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[CH3:30][O:31][CH2:32][CH2:33][N:34]1[C:38]2[CH:39]=[C:40](B3OC(C)(C)C(C)(C)O3)[CH:41]=[CH:42][C:37]=2[S:36][C:35]1=[O:52].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[NH2:1][C:2](=[O:29])[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:40]2[CH:41]=[CH:42][C:37]3[S:36][C:35](=[O:52])[N:34]([CH2:33][CH2:32][O:31][CH3:30])[C:38]=3[CH:39]=2)=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 59568595(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateHCID 595685993-(2-Methoxyethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2(3H)-one

생성물 1

HCID 59568593(S)-tert-Butyl 4-(1-amino-3-(4-(3-(2-methoxyethyl)-2-oxo-2,3-dihydrobenzo[d]thiazol-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate수율 66%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
85 °C

실험 절차

(S)-tert-butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iii), 203 mg) in acetonitrile (7 mL) under nitrogen was treated with 3-(2-methoxyethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2(3H)-one (Example 9, step (ii), 132 mg) followed by aqueous sodium carbonate (2M, 0.392 mL). Nitrogen was bubbled through the mixture and 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (5 mg) was added. The mixture was stirred at 85° C. for 25 h and then allowed to cool. The solution was purified by chromatography on silica using ethyl acetate 50-100% in isohexane as eluent to afford the sub-titled compound (155 mg).

후처리

  1. customNitrogen was bubbled through the mixture and 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (5 mg)
  2. additionwas added
  3. temperatureto cool
  4. customThe solution was purified by chromatography on silica

출처 및 근거

ORD 기록
ord-5805ad39de0f4c19b78818633aabd0f0
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193239B2

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