Hydrochloric Acid → HCID 86593028, compound

HRID 1815553Notes

Reaction equation

HRID 1815553 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:16][C@H:17]2[O:21]C(C)(C)[N:19]([C:24]([O:26][C@H:27]3[C@H:34]4[C@H:30]([O:31][CH2:32][CH2:33]4)[O:29][CH2:28]3)=[O:25])[C@H:18]2[CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([C:50]#[N:51])[CH:45]=3)=[CH:38][CH:37]=2)[CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:16][C@@H:17]([OH:21])[C@@H:18]([NH:19][C:24](=[O:25])[O:26][C@H:27]2[C@H:34]3[C@H:30]([O:31][CH2:32][CH2:33]3)[O:29][CH2:28]2)[CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([C:50]#[N:51])[CH:45]=3)=[CH:38][CH:37]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 86593027HCID 86593027, compound

Product 1

HCID 86593028HCID 86593028, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of (3S,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (4S,5R)-5-{[[(4-aminophenyl)sulfonyl](isobutyl)amino]methyl}-4-{4-[(3-cyanobenzyl)oxy]benzyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate in 3 mL of dioxane was added 4M hydrochloric acid in dioxane (1.5 mL) and water (0.05 mL). The solution was stirred for 1 hour followed by neutralization with 10% aqueous Na2CO3. The solution was extracted with dichloromethane (3×15 mL). The organic phase was dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified on silica gel using ethyl acetate-hexanes (8:2) as eluent to provide 17 mg (61%) of the title compound. 1H-NMR (DMSO-d6): δ 0.74 (3H,d), 0.81(3H,d), 1.18 (1H,m), 1.28 (1H,m), 1.89 (1H,m), 2.35 (1H,t), 2.54-2.60 (2H,m), 2.71 (1H,m), 2.86-2.93 (2H,m), 3.22-3.29 (1H,dd), 3.42-3.48 (1H,m), 3.53-3.59 (3H,m), 3.65 (1H,t), 3.82 (1H,q), 4.80 (1H,q), 4.93 (1H,d,b), 5.07 (2H,s), 5.47 (1H,d), 5.94 (2H,s,b), 6.54 (2H,d), 6.83 (2H,d), 7.08 (2H,d), 7.19 (1H,d), 7.33 (2H,d), 7.56 (1H,t), 7.74 (2H,t), 7.85 (1H,s). MS: 680 (M+).

Workup

  1. extractionThe solution was extracted with dichloromethane (3×15 mL)
  2. dry with materialThe organic phase was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-a726ca37f5204f60a718a2be8998e55c
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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