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Potassium Carbonate → 3-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2,5-dione

HRID 482743
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HRID 482743 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[NH:11][C:10]1=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(N)=C(C(C[C@H](N)C(O)=O)=O)C=1.Br[CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]([CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:10]1=[O:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 161166KynurenineHCID 14666415tert-Butyl (S)-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)carbamate

생성물 1

HCID 100926163-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2,5-dione

시약·촉매·용매 1

HCID 180
Acetone
용매

실험 절차

A solution of 3-(S)-t-butyloxycarbonylamino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2,5-dione (12.5 g) prepared from L-kynurenine as described in Australian J. Chemistry Vol. 33, 633-40 (1980), and t-butyl bromoacetate (10.1 g) in acetone (700 ml) was stirred at room temperature under a dry nitrogen atmosphere. Potassium carbonate (12.5 g) was added in one portion and the resulting suspension was stirred at room temperature for 16 hours. The potassium salts were filtered off and the filtrate evaporated to dryness. The residue was partitioned between ethyl acetate (250 ml) and H2O (250 ml). The layers were separated and the organic phase dried (sodium sulfate). The residue was triturated with petroleum ether (350 ml; bp 30°-60°) to give 3-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2,5-dione, m.p. 75°-77° C., [alpha]D =-172° (C=0.96 in DMF).

후처리

  1. filtrationThe potassium salts were filtered off
  2. customthe filtrate evaporated to dryness
  3. customThe residue was partitioned between ethyl acetate (250 ml) and H2O (250 ml)
  4. customThe layers were separated
  5. dry with materialthe organic phase dried (sodium sulfate)
  6. customThe residue was triturated with petroleum ether (350 ml; bp 30°-60°)

출처 및 근거

ORD 기록
ord-faff96c0a9a640b2b1b20dd72270d430
출처 데이터셋
uspto-grants-1986_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04575503

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