4-Methylmorpholine → tert-butyl-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionate

HRID 1006127노트

반응식

HRID 1006127 반응식
[C:1]([O:5][C:6](=[O:34])[C@H:7]([N:10]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[S:11]([C:14]1[C:19]([CH3:20])=[CH:18][C:17]([O:21][CH3:22])=[CH:16][C:15]=1[CH3:23])(=[O:13])=[O:12])[CH2:8][NH2:9])([CH3:4])([CH3:3])[CH3:2].[C:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N:44]1[CH:48]=[CH:47][CH:46]=[CH:45]1)(O)=[O:36].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.C(N=C=N)CC>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:1]([O:5][C:6](=[O:34])[C@H:7]([N:10]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[S:11]([C:14]1[C:19]([CH3:20])=[CH:18][C:17]([O:21][CH3:22])=[CH:16][C:15]=1[CH3:23])(=[O:12])=[O:13])[CH2:8][NH:9][C:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N:44]1[CH:48]=[CH:47][CH:46]=[CH:45]1)=[O:36])([CH3:4])([CH3:2])[CH3:3]

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 7285212-(1H-pyrrol-1-yl)benzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 18621663Propyl carbodiimide hy-drochlorideHCID 69762296tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-amino-propionate

생성물 1

HCID 69762802tert-butyl-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of tert-butyl-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-amino-propionate (1.02 g, 2.0 mmol), 1-(2-carboxyphenyl)pyrrole (581 mg, 3.1 mmol), 1-hydroxybenzotriazole hydrate (279 mg, 2.0 mmol), N-methylmorpholine (0.8 ml, 7.3 mmol) and 4-dimethylaminopyridine (30 mg, 0.25 mmol) in dry dimethylformamide (25 ml) was added 1-ethyl-3,3-dimethylamino)-propyl carbodiimide hydrochloride salt (600 mg,, 3.1 mmol) and the material was stirred overnight. The dimethylformamide was removed on the rotary evaporator and the residue was taken up in ethyl acetate (80 ml) and partitioned with an equal volume of aqueous hydrochloric acid (1.5%, 80 ml). The organic phase was collected and washed with equal volumes of 5% aqueous sodium bicarbonate and then brine. The aqueous phases were back extracted with ethyl acetate (2×80 ml) and the organic phases combined, dried over magnesium sulfate, filtered and condensed to provide a residue. This material was chromatographed using preparative TLC plates (45% ethyl acetate/hexanes) to afford tert-butyl-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionate) as a pale yellow foamy solid (927 mg).

후처리

  1. customThe dimethylformamide was removed on the rotary evaporator
  2. custompartitioned with an equal volume of aqueous hydrochloric acid (1.5%, 80 ml)
  3. customThe organic phase was collected
  4. washwashed with equal volumes of 5% aqueous sodium bicarbonate
  5. extractionThe aqueous phases were back extracted with ethyl acetate (2×80 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customcondensed
  9. customto provide a residue
  10. customThis material was chromatographed

출처 및 근거

ORD 기록
ord-61866a7db0be407eb28fc51d7fcd0302
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787559B2

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