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Dicyclohexylcarbodiimide → 5-tert-butyloxycarbonylamino acetoxy-12H-benzo[a]phenothiazine

HRID 64964
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인쇄 미리보기

반응식

HRID 64964 반응식
C1(N=C=NC2CCCCC2)CCCCC1.[OH:16][C:17]1[CH:30]=[C:29]2[C:20]([NH:21][C:22]3[C:27]([S:28]2)=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:19]2[CH:31]=[CH:32][CH:33]=[CH:34][C:18]=12.[C:35]([O:39][C:40]([NH:42][CH2:43][C:44](O)=[O:45])=[O:41])([CH3:38])([CH3:37])[CH3:36]>C1COCC1.CN(C1C=CN=CC=1)C>[C:35]([O:39][C:40]([NH:42][CH2:43][C:44]([O:16][C:17]1[CH:30]=[C:29]2[C:20]([NH:21][C:22]3[C:27]([S:28]2)=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:19]2[CH:31]=[CH:32][CH:33]=[CH:34][C:18]=12)=[O:45])=[O:41])([CH3:38])([CH3:37])[CH3:36]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 137124785-hydroxy-12H-benzo[a]phenothiazine

생성물 1

HCID 137124875-tert-butyloxycarbonylamino acetoxy-12H-benzo[a]phenothiazine

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 8028
Tetrahydrofuran
용매

실험 절차

Dicyclohexylcarbodiimide (21 g) was added to a solution of 5-hydroxy-12H-benzo[a]phenothiazine (4.2 g) and N-tert-butyloxycarbonyl glycine (8.4 g) in THF (150 ml) followed by the addition of DMAP (0.2 g). The reaction mixture was stirred for 15 minutes, filtered and the filtrate evaporated to dryness. The residue was dissolved in EtOAc, washed with a solution of NaHCO3, dried and evaporated to dryness. The resulting oily residue was chromatographed on silica gel (5% EtOAc/CH2Cl2) to afford 5-tert-butyloxycarbonylamino acetoxy-12H-benzo[a]phenothiazine. m.p. 175° as an intermediate.

후처리

  1. filtrationfiltered
  2. customthe filtrate evaporated to dryness
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with a solution of NaHCO3
  5. customdried
  6. customevaporated to dryness
  7. customThe resulting oily residue was chromatographed on silica gel (5% EtOAc/CH2Cl2)

출처 및 근거

ORD 기록
ord-c7688d9bdcb5466090708ad794c41ee2
출처 데이터셋
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04611056

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