Water → (E)-(2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-non-6-enoic acid [(3S,6R)-6-(6-amino-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-amide

HRID 2224030Notes

Reaction equation

HRID 2224030 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C@H:11]1[CH2:17][N:16]([CH3:18])[C:15](=[O:19])[C@@H:14]([NH:20][C:21](=[O:37])[C@H:22]([O:35][CH3:36])[C@H:23]([OH:34])[C@@H:24]([OH:33])[C@H:25]([OH:32])/[CH:26]=[CH:27]/[C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:13][CH2:12]1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(Cl)Cl>[NH2:1][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C@H:11]1[CH2:17][N:16]([CH3:18])[C:15](=[O:19])[C@@H:14]([NH:20][C:21](=[O:37])[C@H:22]([O:35][CH3:36])[C@H:23]([OH:34])[C@@H:24]([OH:33])[C@H:25]([OH:32])/[CH:26]=[CH:27]/[C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 59840149(E)-(2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-non-6-enoic acid [(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-amide

Product 1

HCID 59716400(E)-(2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-non-6-enoic acid [(3S,6R)-6-(6-amino-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-amideYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (E)-(2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-non-6-enoic acid [(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-amide (0.13 g, 0.25 mmol) in THF (2 mL) is added H2O and triphenylphosphine (0.120 g, 0.5 mmol). After 8 h the reaction solution is evaporated under vacuum to give a semisolid residue that is dissolved in CH2Cl2 (10 mL), adsorbed on silica and chromatographed (CH2Cl2/NH3 to 25% CH3OH/CH2Cl2/NH3 gradient) to give 0.106 g (85%) of (E)-(2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-non-6-enoic acid [(3S,6R)-6-(6-amino-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-amide as a white solid. MS (ESI) 502.1 (M+H)+

Workup

  1. customAfter 8 h the reaction solution is evaporated under vacuum
  2. customto give a semisolid residue that
  3. customchromatographed (CH2Cl2/NH3 to 25% CH3OH/CH2Cl2/NH3 gradient)

Sources & evidence

ORD record
ord-3945053941e1499b92cd9903ee5bbb5d
Source dataset
uspto-grants-2008_05
Patent number
US07378410B2

Reaction notes

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