Sodium Iodide → 1-Benzyl 4-(tert-Butyl) N-Benzyl-N-(2-(chloromethyl)allyl)-L-aspartate

HRID 61416Notes

Reaction equation

[C:1]([O:5][C:6](=[O:27])[CH2:7][C@H:8]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[Cl:36][CH2:37][C:38]([CH2:40]Cl)=[CH2:39]>CC#N>[C:1]([O:5][C:6](=[O:27])[CH2:7][C@H:8]([N:19]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:40][C:38]([CH2:37][Cl:36])=[CH2:39])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 81 °C

Procedure

A mixture of (2S)-benzylamino-succinic acid 1-benzyl ester 4-tert-butyl ester (12.1 g, 32.6 mmol), K2CO3 (14 g, 3 equiv.), NaI (3.0 g, 20 mmol) and 3-chloro-2-chloromethyl-1-propene (5.1 g, 40.8 mmol) in MeCN (150 mL) was stirred at 81° C. for 16 h. After cooling, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification by Combiflash (hexane and ethyl acetate: gradient 0 to 8% during 12 min) afforded (2S)-[benzyl-(2-chloromethyl-allyl)-amino]-succinic acid 1-benzyl ester 4-tert-butyl ester (8.7 g, 58%). MS (ESI): 458 (M+Na+).

Workup

temperatureAfter cooling
filtrationthe reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customPurification by Combiflash (hexane and ethyl acetate: gradient 0 to 8% during 12 min)

Sources & evidence

ORD record: ord-0aa6f41428f748ed803e2853f83968ea
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440958B2

Reaction notes

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