Water → tert-butyl 2-(4-amino-N-(4-(5-(4-methylphenylsulfonamido)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetate

HRID 923614Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:43]=[CH:42][C:20]([CH2:21][N:22]([CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:23](=[O:33])[C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]([N:22]([CH2:34][C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])[CH2:21][C:20]2[CH:19]=[CH:18][C:17]([C:14]3[N:13]=[C:12]([NH:11][S:8]([C:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=4)(=[O:10])=[O:9])[O:16][N:15]=3)=[CH:43][CH:42]=2)=[O:33])=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Prepared using General Procedure 5. To a stirred solution of tert-butyl 2-(N-(4-(5-(4-methylphenylsulfonamido)-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate INT-68 (20 mg, 0.033 mmol) in THF (3 mL) and water (1 mL) was added sodium dithionite (17.2 mg, 0.099 mmol) and heated to 65° C. for 2 h. The reaction mixture was extracted with EA (10 mL) and washed with brine (10 mL). The organics were concentrated in vacuo to afford 13 mg (65%) of tert-butyl 2-(4-amino-N-(4-(5-(4-methylphenylsulfonamido)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetate INT-69 as a white solid. LCMS-ESI (m/z) calculated for C29H31N5O6S: 577; found 576 [M−H]−, tR=2.41 min (Method 5).

Workup

customPrepared
extractionThe reaction mixture was extracted with EA (10 mL)
washwashed with brine (10 mL)
concentrationThe organics were concentrated in vacuo

Sources & evidence

ORD record: ord-9db3042b2cb142ca8ab76e42571b3f4d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278910B2

Reaction notes

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