Lithium Hydroxide → HCID 131719311, compound

HRID 54164Notes

Reaction equation

[C:1]1([CH2:7][NH:8][C:9]([NH:11][C@H:12]([C:16]([NH:18][C@H:19]([C:21]([O:23]C)=[O:22])[CH3:20])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-]>>[C:1]1([CH2:7][NH:8][C:9]([NH:11][C@H:12]([C:16]([NH:18][C@H:19]([C:21]([OH:23])=[O:22])[CH3:20])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 131719310HCID 131719310, compound

Product 1

HCID 131719311HCID 131719311, compound

Procedure

By the same procedure used to prepare the title compound of Example 1C, PhCH2NHCOValAlaOCH3 (671 mg, 2.00 mmole) and LiOH.OH (168 mg, 4.00 mmole) in 10% aqueous CH3OH (20 mL) gave after quenching with sulfonic acid ion exchange resin (18.0 g, 40 meq) 658 mg (100%) of pure product as an off-white flaky solid. Recyrstallization of a portion from ethyl acetate/CH3OH gave an analytical sample as very fine white crystals: mp 205°-206° C.; 1H NMR (DMSO-d6) δ 0.79 (d, J=6.8 Hz, 3H), 0.86 (d, J=6.7 Hz, 3H), 1.25 (d, J=7.3 Hz, 3H), 1.85-2.0 (m, 1H), 4.05-4.3 (m, 4H), 6.09 (d, J=9.3 Hz, 1H), 6.54 (t, J=6.0 Hz, 1H), 7.15-7.35 (m, 5H), 824 (d, J=7.0 Hz, 1H); MS (LSIMS) m/e 344 (22, M+ +Na), 322 (83, M+ +1), 233 (70), 205(18), 189 (100); [α]D20 +15.3° (c=1.0, DMF); Analysis calculated for C16H23N3O4 : C, 59.79; H, 7.21; N, 13.08; found: C, 59.87; H, 7.30; N, 12.80.

Sources & evidence

ORD record: ord-e5453b9b10f443babb307de9382c8bbd
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05622830

Reaction notes

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