Boc-L-Valine → HCID 10377208, compound

HRID 855883Notes

Reaction equation

C(OC([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.[F:16][C:17]1([F:33])[C@H:21]([CH3:22])[N:20](C(=O)[C@H](CC(C)C)N)[C@H:19]([C:31]#[N:32])[CH2:18]1>>[F:16][C:17]1([F:33])[C@H:21]([CH3:22])[N:20]([C:13](=[O:15])[C@H:9]([CH:10]([CH3:11])[CH3:12])[NH2:8])[C@H:19]([C:31]#[N:32])[CH2:18]1

Participants

Reactant 2

HCID 83693Boc-L-Valine

HCID 10445273HCID 10445273, compound

Product 1

HCID 10377208HCID 10377208, compound

Procedure

This compound was prepared from 51 mg (0.23 mmol) of (S)-N-tert-butoxycarbonylvaline and 50 mg (0.23 mmol) of (2,5-cis) 4,4-difluoro-5-methyl-pyrrolidine-2-carboxylic acid methyl ester hydrochloride (Example 95G) according to the same five step sequence as for (2S,5S)-4,4-difluoro-1-L-leucyl-5-methylpyrrolidine-2-carbonitrile (example 95H through example 95L) to give the titled compound as a colorless foam. 1H NMR (500 MHz, DMSO-d6) (mixture of rotamers, major rotamer only) δ ppm 0.99 (m, 6H) 1.37 (m, 3H) 2.11 (m, 1H) 2.96 (m, 1H) 3.09 (m, 1H) 4.09 (bs, 1H) 4.65 (m, 1H) 5.06 (t, J=8.6 Hz, 1H) 8.31 (bs, 3H) MS (ESI) m/z=246 (M+H)+.

Sources & evidence

ORD record: ord-eb4692d898a548d68b7dbb7d3f721513
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262207B2

Reaction notes

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