Aniline → HCID 57224651, compound

HRID 1899007Notes

Reaction equation

HRID 1899007 reaction equation
C(N(C(C)C)CC)(C)C.Cl[Si](C)(C)C.Cl.[NH2:16][C:17]1[CH:18]=[C:19]([CH:32]=[CH:33][CH:34]=1)[C:20]([NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24])=[O:21].[C:35]([S:38][CH:39]1[CH2:43][N:42]([C:44]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][C:51]([N+:54]([O-:56])=[O:55])=[CH:50][CH:49]=2)=[O:45])[CH:41]([C:57](O)=[O:58])[CH2:40]1)(=[O:37])[CH3:36].CN1CCOCC1.ClC(OCC(C)C)=O.NC1C=CC=CC=1>C1COCC1>[C:35]([S:38][C@@H:39]1[CH2:43][N:42]([C:44]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][C:51]([N+:54]([O-:56])=[O:55])=[CH:50][CH:49]=2)=[O:45])[C@H:41]([C:57](=[O:58])[NH:16][C:17]2[CH:34]=[CH:33][CH:32]=[C:19]([C:20](=[O:21])[NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:18]=2)[CH2:40]1)(=[O:37])[CH3:36]

Participants

9

Reactant 7

HCID 6115AnilineHCID 6397ChlorotrimethylsilaneHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 135043244-Acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-carboxypyrrolidineHCID 23372561HCID 23372561, compound

Product 1

HCID 57224651HCID 57224651, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

Di-isopropylethylamine (2.0 ml) followed by chlorotrimethylsilane (0.73 ml) was added to a stirred solution of 3-amino-N-phenylsulfonylbenzamide hydrochloride (1.8 g, 5.7 mM) in THF (distilled from CaH2 ; 25 ml) under an argon atmosphere. The solution was allowed to stand for 30 minutes then cooled to -10 C. Meanwhile 4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-carboxypyrrolidine (1.84 g, 5 mM) dissolved in tetrahydrofuran (25 ml) was treated with N-methylmorpholine (1.1 ml, 10 mM). This solution was cooled to -15° C. with stirring under an argon atmosphere, and treated with isobutyl chloroformate (0.66 ml, 5 mM) in one portion. After 20 minutes, this solution was added to the solution of the trimethylsilyl derivative of the aniline (prepared above). When the addition was complete, the mixture was stirred for 15 minutes and the solvent evaporated. The residue was partitioned between ethyl acetate (200 ml) and 1M aqueous hydrochloric acid (100 ml). The ethyl acetate layer was washed with hydrochloric acid, brine and dried giving (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(3-phenylsulfonylcarbamoylphenylcarbamoyl)pyrrolidine as a gum which was crystallised from EtOH (2.3 g).

Workup

  1. temperaturethen cooled to -10 C
  2. waitAfter 20 minutes
  3. additionWhen the addition
  4. stirringthe mixture was stirred for 15 minutes
  5. customthe solvent evaporated
  6. customThe residue was partitioned between ethyl acetate (200 ml) and 1M aqueous hydrochloric acid (100 ml)
  7. washThe ethyl acetate layer was washed with hydrochloric acid, brine
  8. customdried

Sources & evidence

ORD record
ord-37fc0b70f23447f6bf33fd5f251c258b
Source dataset
uspto-grants-1996_11
Patent number
US05571805

Reaction notes

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