Acetic Anhydride → 3(S)-Isopropyl-5(S)-{1 (S)-azido-3(S)-isopropyl-4(R,S)-acetoxy-4-[4-(3-benzyloxypropyloxy)-3-(3-methoxypropyloxy)-phenyl]-butyl}-tetrahydrofuran-2-one

HRID 1779813Notes

Reaction equation

HRID 1779813 reaction equation
[CH:1]([C@@H:4]1[CH2:8][C@@H:7]([C@@H:9]([N:41]=[N+:42]=[N-:43])[CH2:10][C@@H:11]([CH:38]([CH3:40])[CH3:39])[CH:12]([OH:37])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:15]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH:14]=2)[O:6][C:5]1=[O:44])([CH3:3])[CH3:2].[C:45](OC(=O)C)(=[O:47])[CH3:46]>N1C=CC=CC=1>[CH:1]([C@@H:4]1[CH2:8][C@@H:7]([C@@H:9]([N:41]=[N+:42]=[N-:43])[CH2:10][C@@H:11]([CH:38]([CH3:39])[CH3:40])[CH:12]([O:37][C:45](=[O:47])[CH3:46])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[C:15]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH:14]=2)[O:6][C:5]1=[O:44])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1317195743(S)-Isopropyl-5(S)-{1(S)-azido-3(S)-isopropyl-4(R,S)-hydroxy-4-(4-(3-benzyloxy-propyloxy)-3-(3-methoxypropyloxy)phenyl]-butyl}-tetrahydrofuran-2-one

Product 1

HCID 1317195753(S)-Isopropyl-5(S)-{1 (S)-azido-3(S)-isopropyl-4(R,S)-acetoxy-4-[4-(3-benzyloxypropyloxy)-3-(3-methoxypropyloxy)-phenyl]-butyl}-tetrahydrofuran-2-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 144 mg of 3(S)-isopropyl-5(S)-{1(S)-azido-3(S)-isopropyl-4(R,S)-hydroxy-4-[4-(3-benzyloxypropyloxy)-3-(3-methoxypropyloxy)-phenyl]-butyl}-tetrahydrofuran-2-one in 1.8 ml of acetic anhydride and 0.057 ml of pyridine is stirred for 30 hours at room temperature and is then concentrated to dryness by evaporation at room temperature and under reduced pressure. The residue is partitioned between dichloromethane (3×) and water/saturated sodium chloride solution (3×). The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation, and the residue is purified by means of FC (hexane/ethyl acetate=4:1), yielding the title compound: Rf (hexane/ethyl acetate=2:1)=0.38 and 0.33; HPLC Rt =21.76 and 21.82 minutes (diastereoisomeric mixture); FAB-MS M+ =653, (M+Na)+ =676.

Workup

  1. concentrationis then concentrated to dryness by evaporation at room temperature and under reduced pressure
  2. customThe residue is partitioned between dichloromethane (3×) and water/saturated sodium chloride solution (3×)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. customthe residue is purified by means of FC (hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-dd7efcf7afde47e4b7bed441fbd1917b
Source dataset
uspto-grants-1997_05
Patent number
US05627182

Reaction notes

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