Diisopropylethylamine → HCID 69224755, compound

HRID 1166484Notes

Reaction equation

HRID 1166484 reaction equation
[CH2:1]([C@H:8]([NH:30][C:31](=[O:38])[O:32][CH:33]1[CH2:37][CH2:36][O:35][CH2:34]1)[C@@H:9]([OH:29])[CH:10]([NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[O:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C@@H](CC1C=CC=CC=1)[C@H](O)CN(OC1CCCC1)S(C1C=CC(OC)=CC=1)(=O)=O.C(N(CC)C(C)C)(C)C>>[CH2:1]([C@H:8]([NH:30][C:31](=[O:38])[O:32][C@H:33]1[CH2:37][CH2:36][O:35][CH2:34]1)[C@@H:9]([OH:29])[CH:10]([NH:17][S:18]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)(=[O:20])=[O:19])[O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 57010648N1-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N1-(cyclopentyloxy)-4-methoxy-1-benzenesulfonamideHCID 86585032tetrahydro-3-furanyl N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(4-methoxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

Product 1

HCID 69224755HCID 69224755, compoundYield 87%

Procedure

tetrahydro-3-furanyl N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(4-methoxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate. A mixture of 2,5-dioxo-1-pyrrolidinyl [(3S)tetrahydro-3-furanyl]carbonate (13.8 mg, 0.0602 mmol, W094/05639), N1-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N1-(cyclopentyloxy)-4-methoxy-1-benzenesulfonamide x trifluoracetic acid (Step 1, Example 48), (30 mg, 0.0547 mmol), and N,N-diisopropylethylamine (23.8 AL, 0.137 mmol) were combined at ambient temperature under an Argon atmosphere. After stirring for 18 hours, the reaction mixture was evaporated in vacuo to a residue and purified on a preparative silica gel TLC plate (20x20 cm, 500 WM) eluting with 96:4 chloroform : methanol. The product band was removed, eluted with 3:1 methylene chloride methanol, filtered, evaporated in vacuo and dried under high vacuum to provide (3S)tetrahydro-3-furanyl N-((1S,2R) -1-benzyl-3-(cyclopentyloxy)[(4-methoxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate (26 mg, 87%) as a foam. H1-NMR (chloroform-D3): 1.73 (m, 9H), 2.14 (m, 1H), 2.92 (m, 5H), 3.77 (m, 6H), 3.87 (s, 3H), 4.79 (bm, 2H), 5.10 (bs, 1H), 6.97 (d, 2H), 7.23 (m, 5H), 7.70 (d, 2H). MS(ESI): 571 (M+Na).

Workup

  1. customwere combined at ambient temperature under an Argon atmosphere
  2. customthe reaction mixture was evaporated in vacuo to a residue
  3. custompurified on a preparative silica gel TLC plate (20x20 cm, 500 WM)
  4. washeluting with 96:4 chloroform
  5. customThe product band was removed
  6. washeluted with 3:1 methylene chloride methanol
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-89e506d30dd145d5b43d1ee9a690d443
Source dataset
uspto-grants-2003_09
Patent number
US06613743B2

Reaction notes

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