Trifluoroacetic acid → HCID 86634087, compound

HRID 1688142Notes

Reaction equation

C([O:5][C:6](=[O:20])[CH2:7][NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[NH2:19])(C)(C)C.[C:21](O)([C:23]([F:26])([F:25])[F:24])=[O:22]>>[NH2:19][C:11]1[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=1[CH2:9][N:8]([CH2:7][C:6]([OH:5])=[O:20])[C:21](=[O:22])[C:23]([F:26])([F:25])[F:24]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67263649HCID 67263649, compound

Product 1

HCID 86634087HCID 86634087, compound

Procedure

A solution of (2-amino-4-nitro-benzylamino)-acetic acid tert-butyl ester (0.28 g, 1.0 mmol) was heated at 120° C. for 16 hours in TFA (5 mL). Concentration and chromatography on silica gel with methylene chloride and methanol (20:1) gave 0.3 g of [(2-amino-4-nitro-benzyl)-(2,2,2-trifluoro-acetyl)-amino]-acetic acid. Following a procedure analogous to Example 1848d, [(2-amino-4-nitro-benzyl)-(2,2,2-trifluoro-acetyl)-amino]-acetic acid was converted to 8-nitro-4-(2,2,2-trifluoro-acetyl)-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one: 1H NMR (300 MHz, CD3OD) δ 8.0 (m, 2H), 7.6 (dd, 1H), 4.98 (s, 1H), 4.57 (s, 2H), 4.53 (s, 1H).

Workup

concentrationConcentration and chromatography on silica gel with methylene chloride and methanol (20:1)

Sources & evidence

ORD record: ord-c8ea64a754b54acab83fa9bd146ff743
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

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