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N-Acetylsulfanilyl chloride → [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(1S,2R)-3-[(4-acetamidophenyl)sulfonyl-(4-cyano-2,2-dimethyl-butyl)amino]-1-benzyl-2-hydroxy-propyl]carbamate

HRID 1167259
Notes
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Reaction equation

HRID 1167259 reaction equation
[O:1]1[C@H:5]2[O:6][CH2:7][CH2:8][C@H:4]2[C@@H:3]([O:9][C:10](=[O:32])[NH:11][C@@H:12]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:13]([OH:24])[CH2:14][NH:15][CH2:16][C:17]([CH3:23])([CH3:22])[CH2:18][CH2:19][C:20]#[N:21])[CH2:2]1.C(N(C(C)C)CC)(C)C.[C:42]([NH:45][C:46]1[CH:51]=[CH:50][C:49]([S:52](Cl)(=[O:54])=[O:53])=[CH:48][CH:47]=1)(=[O:44])[CH3:43]>C(Cl)Cl>[O:1]1[C@H:5]2[O:6][CH2:7][CH2:8][C@H:4]2[C@@H:3]([O:9][C:10](=[O:32])[NH:11][C@@H:12]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@H:13]([OH:24])[CH2:14][N:15]([S:52]([C:49]2[CH:48]=[CH:47][C:46]([NH:45][C:42](=[O:44])[CH3:43])=[CH:51][CH:50]=2)(=[O:54])=[O:53])[CH2:16][C:17]([CH3:22])([CH3:23])[CH2:18][CH2:19][C:20]#[N:21])[CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8481N-Acetylsulfanilyl chlorideHCID 81531DiisopropylethylamineHCID 59815752[(1S, 2R)-1-Benzyl-3-(4-cyano-2,2-dimethylbutylamino)-2-hydroxy-propyl]-carbamic acid (3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-yl ester

Product 1

HCID 480326[(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(1S,2R)-3-[(4-acetamidophenyl)sulfonyl-(4-cyano-2,2-dimethyl-butyl)amino]-1-benzyl-2-hydroxy-propyl]carbamate
Yield 18.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(1S,2R)-1-Benzyl-3-(4-cyano-2,2-dimethyl-butylamino)-2-hydroxy-propyl]-carbamic acid (3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-yl ester (0.020 g, 0.05 mmol) was dissolved in CH2Cl2 and treated with diisopropylethylamine (0.016 ml, 0.09 mmol) and 4-acetamidobenzenesulfonyl chloride (0.011 g, 0.05 mmol) at ambient temperature under argon with stirring. After 15 h the reaction mixture was concentrated in vacuo, taken up in EtOAc, washed with sat. aq. NaHCO3, and brine. The organic phase was dried over MgSO4, filtered and solvent removed in vacuo. Purification by preparative thin layer chromatography (EtOAc) gave 0.006 g of a white solid. MS (ES): 643 (M+1).

Workup

  1. concentrationAfter 15 h the reaction mixture was concentrated in vacuo
  2. washwashed with sat. aq. NaHCO3, and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customsolvent removed in vacuo
  6. customPurification by preparative thin layer chromatography (EtOAc)

Sources & evidence

ORD record
ord-b40d0f8f8a3648cfba2de333d308e27b
Source dataset
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06617350B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes