tert-butyl (5R)-5-(acetoxy)hexanoate → (1S,2E)-3-{(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-3,5-dihydroxycyclopentyl}-1-(2-phenylethyl)prop-2-en-1-yl (5R)-5-(nitrooxy)hexyl carbonate

HRID 422896Notes

Reaction equation

HRID 422896 reaction equation
C([O:4][C@H:5]([CH3:16])[CH2:6][CH2:7][CH2:8][C:9]([O:11][C:12](C)(C)C)=O)(=O)C.C(=O)([O-])OC1C=CC([N+:25]([O-:27])=[O:26])=CC=1.[CH3:30][CH2:31][NH:32][C:33]([CH2:35][CH2:36][CH2:37]/[CH:38]=[CH:39]\[CH2:40][C@@H:41]1[C@@H:45](/[CH:46]=[CH:47]/[C@@H:48]([OH:57])[CH2:49][CH2:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C@H:44]([OH:58])[CH2:43][C@@H:42]1[OH:59])=[O:34].B([O-])[O-:61]>>[C:12](=[O:61])([O:11][CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]([O:4][N+:25]([O-:27])=[O:26])[CH3:16])[O:57][C@@H:48]([CH2:49][CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)/[CH:47]=[CH:46]/[C@H:45]1[C@H:44]([OH:58])[CH2:43][C@H:42]([OH:59])[C@@H:41]1[CH2:40]/[CH:39]=[CH:38]\[CH2:37][CH2:36][CH2:35][C:33]([NH:32][CH2:31][CH3:30])=[O:34]

Participants

4

Reactant 3

HCID 11117869tert-butyl (5R)-5-(acetoxy)hexanoateHCID 21864993p-Nitrophenyl carbonateHCID 178465099HCID 178465099, compound

Product 1

HCID 58231638(1S,2E)-3-{(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-3,5-dihydroxycyclopentyl}-1-(2-phenylethyl)prop-2-en-1-yl (5R)-5-(nitrooxy)hexyl carbonate

Procedure

Similar to Example R-1, except started Scheme R with antipodal tert-butyl (5R)-5-(acetoxy)hexanoate (Pamies, O.; Backvall, J.-E. J. Org. Chem. 2002, 67, 1261-1265) and eventually prepared antipode of crude p-nitrophenyl carbonate r-4, which was similarly used to acylate bimatoprost boronate (580 mg, 1.2 mmol) to provide after preparative HPLC purification, 420 mg (57%) of 15-acyl nitrate R-2.

Workup

  1. customto provide
  2. customafter preparative HPLC purification, 420 mg (57%) of 15-acyl nitrate R-2

Sources & evidence

ORD record
ord-7f1bfdd63ab448a0bfe89e4ebd211194
Source dataset
uspto-grants-2012_01
Patent number
US08101658B2

Reaction notes

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