N-Hydroxyphthalimide → HCID 66773026, compound

HRID 642937Notes

Reaction equation

HRID 642937 reaction equation
[CH2:1]([O:8][CH:9]1[C:13]([CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:14][OH:15])[O:12][CH:11]([O:25][CH3:26])[CH:10]1[OH:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([O:8][CH:9]1[CH:10]([OH:27])[CH:11]([O:25][CH3:26])[O:12][C:13]1([CH2:14][O:15][N:29]1[C:33](=[O:34])[C:32]2[C:31](=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:30]1=[O:39])[CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66773260HCID 66773260, compound

Product 1

HCID 66773026HCID 66773026, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The O-phthalimido compound is prepared following the reference cited and the procedures illustrated in Example 13 above. The reaction can be adjusted to preferentially react at the primary hydroxyl e.g. the 4′-C-hydroxymethyl group (Bhat, B., et. al., J. Org. Chem. 1996, 61, 8186-8199). Generally, a solution of 21 (1 eq.), N-hydroxyphthalimide (1.1 eq.), and triphenylphosphine (1.1 eq.) in anhydrous tetrahydrofuran is treated with diethyl azodicarboxylate (1.1 eq.). After several hours at room temperature, the mixture is concentrated and subjected to silica gel chromatography to give Compound 22.

Workup

  1. customThe reaction
  2. waitAfter several hours at room temperature
  3. concentrationthe mixture is concentrated

Sources & evidence

ORD record
ord-f829c56a72a34c1eb8476d01a1a8c4b4
Source dataset
uspto-grants-2010_04
Patent number
US07696345B2

Reaction notes

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