Ethyl Acetate → (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-1-benzyl-3-((cyclopentyloxy)[3-(2-morpholinoethoxy)phenyl]sulfonylamino)-2-hydroxypropyl]carbamate

HRID 1166494Notes

Reaction equation

HRID 1166494 reaction equation
[CH2:1]([C@H:8]([NH:37][C:38](=[O:48])[O:39][C@@H:40]1[C@H:47]2[C@H:43]([O:44][CH2:45][CH2:46]2)[O:42][CH2:41]1)[C@H:9]([OH:36])[CH2:10][N:11]([O:30][CH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)[S:12]([C:15]1[CH:20]=[CH:19][C:18](OCCN2CCOCC2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:49]([O:52][CH2:53][CH3:54])(=O)[CH3:50]>>[CH2:1]([C@H:8]([NH:37][C:38](=[O:48])[O:39][C@@H:40]1[C@H:47]2[C@H:43]([O:44][CH2:45][CH2:46]2)[O:42][CH2:41]1)[C@H:9]([OH:36])[CH2:10][N:11]([O:30][CH:31]1[CH2:32][CH2:33][CH2:34][CH2:35]1)[S:12]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([O:36][CH2:9][CH2:8][N:37]2[CH2:54][CH2:53][O:52][CH2:49][CH2:50]2)[CH:20]=1)(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 21356324(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-1-benzyl-3-((cyclopentyloxy)[4-(2-morpholinoethoxy)phenyl]sulfonylamino)-2-hydroxypropyl]carbamate

Product 1

HCID 86585038(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-1-benzyl-3-((cyclopentyloxy)[3-(2-morpholinoethoxy)phenyl]sulfonylamino)-2-hydroxypropyl]carbamate

Procedure

This compound was prepared from Example 44 under the same conditions used for the preparation of Example 98 (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-1-benzyl-3-((cyclopentyloxy)[4-(2-morpholinoethoxy) phenyl]sulfonylamino)-2-hydroxypropyl]carbamate. Rf=0.15 (ethyl acetate); H1-NMR (CDCl3): δ7.44-7.14 (10H,m), 5.62 (1H,s), 5.00 (1H,m), 4.79 (2H,m), 4.16 (2H,m), 3.98-3.60 (10H,m), 3.12 (1H,bs), 3.02-2.71 (8H,m), 2.58 (4H,m), 1.90-1.72 (4H,m), 1.72-1.42 (4H,m); MS (ESI): M+H=690.

Workup

  1. customThis compound was prepared from Example 44 under the same conditions

Sources & evidence

ORD record
ord-98778ab63ad84dc99b038b51e3819ae4
Source dataset
uspto-grants-2003_09
Patent number
US06613743B2

Reaction notes

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