Phthalimide → (+/-)-n-(Tert-butoxycarbonyl)-2-(phthalimidoethyl)glycine allyl ester

HRID 1838408Notes

Reaction equation

HRID 1838408 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([O:16][C:17](=[O:30])[C@H:18]([CH2:27][CH2:28]O)[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:14]=[CH2:15].[C:31]1(=[O:41])[NH:35][C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH2:13]([O:16][C:17](=[O:30])[CH:18]([CH2:27][CH2:28][N:35]1[C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]2[C:31]1=[O:41])[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:14]=[CH2:15]

Participants

5

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12042107(+/-)-N-(tert-butoxycarbonyl)homoserine allyl ester

Product 1

HCID 18753589(+/-)-n-(Tert-butoxycarbonyl)-2-(phthalimidoethyl)glycine allyl esterYield 73%

Procedure

Diethyl azodicarboxylate (5.7 ml, 36.2 mmol, abbreviated as DEAD hereinafter) was added dropwise to a mixture of (±)-N-(tert-butoxycarbonyl)homoserine allyl ester (7.79 g, 30.0 mmol), phthalimide (4.41 g, 30 mmol), triphenylphosphine (9.45 g, 36.0 mmol) and tetrahydrofuiran (75 ml) at room temperature with stirring. This mixture was stirred for 1 hour. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=4/1 as the eluent to afford the desired compound (8.46 g, yield 73%) as a white powder.

Workup

  1. stirringThis mixture was stirred for 1 hour
  2. customThe solvent of the reaction mixture was evaporated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-915a20ccf6704d60b08d33e69fa988cc
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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