N-Hydroxyphthalimide → HCID 59873668, compound

HRID 1698928Notes

Reaction equation

HRID 1698928 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:8][CH:7]=1.O[N:33]1[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]2[C:34]1=[O:43].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[O:43]=[C:34]1[C:35]2[C:36](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37](=[O:38])[N:33]1[O:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:21][C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23])[C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 59873686HCID 59873686, compound

Product 1

HCID 59873668HCID 59873668, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl (2S)-3-[4-(3-hydroxypropoxy)phenyl]-2-[(phenylmethoxy)carbonylamino]propanoate (0.215 g, 0.5 mmol), as prepared in the preceding step, N-hydroxyphthalimide ((0.098 g, 0.6 mmol), and triphenylphosphine (0.157 g, 0.6 mmol) in anhydrous tetrahydrofuran (10 mL) was treated with diethyl azodicarboxylate (0.095 g, 0.6 mmol). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was evaporated to dryness and the residue was placed on a silica gel column (10 g Waters Sep-Pak) and eluted with 20% ethyl acetate and 80% hexane. The pure fractions were combined and evaporated to give the title compound (0.280 g, 97% yield). 1H NMR (300 MHz, CDCl3) δ7.84 (dd, J=5.6,3.0 Hz, 2H), 7.75 (dd, J=5.6, 3.0 Hz, 2H), 7.28-7.34 (m, 5H), 7.03 (d, J=8.7 Hz, 2H), 6.83 (d, J=8.7 Hz, 2H), 5.22 (br d, J=8.2 Hz, 1H), 5.09 (d, J=2.5 Hz, 2H), 4.48 (m, 1 H), 4.41 (t, J=6.3 Hz, 2H), 4.20 (t, J=6.2 Hz, 2H), 3.01 (br d, J=5.9 Hz, 2H), 2.23 (p, J=6.2 Hz, 2H), 1.41 (s, 9H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. washeluted with 20% ethyl acetate and 80% hexane
  3. customevaporated

Sources & evidence

ORD record
ord-cac815d5f38e4abb8bd09ce5c60f9070
Source dataset
uspto-grants-2002_02
Patent number
US06344484B1

Reaction notes

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