Toluene → (S)-7-(((benzyloxy)carbonyl)amino)-7-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)heptanoic acid

HRID 2202560Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:25]1[O:26][C:27]([C:30]2[C:31]([O:40][CH3:41])=[N:32][C:33]3[C:38]([CH:39]=2)=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:28][N:29]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1.CCOCC>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:25]1[O:26][C:27]([C:30]2[C:31]([O:40][CH3:41])=[N:32][C:33]3[C:38]([CH:39]=2)=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:28][N:29]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of F4 in DCM (0.11 M) cooled to 0° C. TFA (15 eq.) was slowly added. The reaction mixture was stirred at 0° C. for 3 days. The solvent was evaporated to afford an oily residue that was co-evaporated first with toluene then with Et2O to give the title compound as a pale yellow solid which was used directly in the next step. MS (ES+) C28H29N3O6: 504 (M+H)+.

Workup

customThe solvent was evaporated
customto afford an oily residue that

Sources & evidence

ORD record: ord-300d30553e53404d8a825958c29c31d7
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365541B2

Reaction notes

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