(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-{(1-ethylpropoxy)[(4-nitrophenyl)sulfonyl]amino}-2-hydroxypropylcarbamate → (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[[(4-aminophenyl)sulfonyl](1-ethylpropoxy)amino]-1-benzyl-2-hydroxypropylcarbamate

HRID 29214Notes

Reaction equation

HRID 29214 reaction equation
[CH2:1]([C@H:8]([NH:31][C:32](=[O:42])[O:33][C@@H:34]1[C@H:41]2[C@H:37]([O:38][CH2:39][CH2:40]2)[O:36][CH2:35]1)[C@H:9]([OH:30])[CH2:10][N:11]([O:24][CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[S:12]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([N:11]([O:24][CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH2:10][C@@H:9]([OH:30])[C@@H:8]([NH:31][C:32](=[O:42])[O:33][C@@H:34]2[C@H:41]3[C@H:37]([O:38][CH2:39][CH2:40]3)[O:36][CH2:35]2)[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:14])=[O:13])=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 59787925(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-{(1-ethylpropoxy)[(4-nitrophenyl)sulfonyl]amino}-2-hydroxypropylcarbamate

Product 1

HCID 59090562(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[[(4-aminophenyl)sulfonyl](1-ethylpropoxy)amino]-1-benzyl-2-hydroxypropylcarbamateYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-{(1-ethylpropoxy)[(4-nitrophenyl)sulfonyl]amino}-2-hydroxypropylcarbamate (237 mg, 0.390 mmol) in absolute methanol (5 mL) was combined with Palladium on carbon (10 wt %, 50 mg) and reduced under a Hydrogen atmosphere over 16 hours. The reaction was filtered and evaporated in vacuo. The residue was purified on silica gel eluting with 50-60% ethyl acetate in hexane. Fractions containing the product were combined and evaporated in vacuo. The residue was triturated with water, filtered and dried under high vacuum to provide (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[[(4-aminophenyl)sulfonyl](1-ethylpropoxy)amino]-1-benzyl-2-hydroxypropylcarbamate (160 mg, 71%) as a white solid. H1-NMR (chloroform-D3): 0.90 (m, 6H), 1.58 (m, 7H), 2.95 (m, 5H), 3.69 (m, 2H), 3.91 (m, 4H), 4.13 (m, 1H), 4.26 (b, 2H), 4.80 (d, 1H), 5.00 (m, 1H), 5.63 (d, 1H), 6.67 (d, 2H), 7.22 (m, 5H), 7.58 (d, 2H).). MS(ESI): 600(M+Na).

Workup

  1. filtrationThe reaction was filtered
  2. customevaporated in vacuo
  3. customThe residue was purified on silica gel eluting with 50-60% ethyl acetate in hexane
  4. additionFractions containing the product
  5. customevaporated in vacuo
  6. customThe residue was triturated with water
  7. filtrationfiltered
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-f1e78bafd117489f8c22674bfb360bab
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Reaction notes

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