Hydrochloric Acid → HCID 69974009, compound

HRID 481258Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[C:53]([C:57]([F:60])([F:59])[F:58])[CH:52]=1)[C:12]1[C:17](=[O:18])[N:16]2[C@H:19]([C:34](N(C(OC(C)(C)C)=O)C3C=CC=CC=3)=[O:35])[CH2:20][C@:21]([CH2:23][C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])([CH3:22])[C:15]2=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.[Li+].[OH-].[O-:65]S([O-])=O.[Na+].[Na+].Cl>O.C1COCC1>[CH2:1]([O:8][C:9]([N:11]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[C:53]([C:57]([F:60])([F:58])[F:59])[CH:52]=1)[C:12]1[C:17](=[O:18])[N:16]2[C@H:19]([C:34]([OH:35])=[O:65])[CH2:20][C@:21]([CH2:23][C:24]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:25])([CH3:22])[C:15]2=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 117d (537 mg, 0.651 mmol) in 4:1 THF/H20 at 0° C., were added 30% H2O2 (0.295 mL, 2.604 mmol) and 1M LiOH (1.107 mL, 1.107 mmol). The mixture was stirred at 0° C. for 2 h, then a solution of Na2SO3 (140 mg, 1.107 mmol) in 1 mL H2O was added dropwise. The mixture was poured into 0.5 M HCl and the product was extracted with EtOAc. The organic was washed with brine, dried (Na2SO4), and concentrated to afford 527 mg of 117e, which was contaminated with BocNHPh. The mixture was used as is in the following step. MS(ESI) 650.3 (M+H+); 648.3 (M−H+).

Workup

extractionthe product was extracted with EtOAc
washThe organic was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-b0488b6c9d1841f0809c3836fc9e2b8a
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653295B2

Reaction notes

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