Benzoic Acid → HCID 54357787, compound

HRID 1941140Notes

Reaction equation

HRID 1941140 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[O:6][C:7]3[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=3[C:9]([N:11]3[CH2:19][C@H:18]4[N:14]([CH2:15][C@@H:16](O)[CH2:17]4)[CH2:13][CH2:12]3)=[N:10][C:4]=2[CH:3]=1.[C:27](O)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[O:6][C:7]3[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=3[C:9]([N:11]3[CH2:19][C@H:18]4[N:14]([CH2:15][C@H:16]([C:27](=[O:34])[C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH2:17]4)[CH2:13][CH2:12]3)=[N:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53748709HCID 53748709, compound

Product 1

HCID 54357787HCID 54357787, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-chloro-11-[(6S,8S)-8-hydroxy-1,4-diazabicyclo[4.3.0]non-4-yl]-dibenz[b,f]-1,4-oxazepine (64 mg, 0.173 mmol), benzoic acid (42.3 mg, 0.346 mmol) and triphenylphosphine (91.0 mg, 0.346 mmol) in anhydrous methylene chloride (20 mL) at 0° C. under argon was added diethyl azodicarboxylate (60.3 mg, 0.346 mmol) via syringe. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The product was absorbed onto silica gel and purified by flash column chromatography using 10% acetone in hexanes as the eluent to give 51.6 mg (63%) of 8-chloro-11-[(6S,8R)-8-benzoyl-1,4-diazabicyclo[4.3.0]non-4-yl]-dibenz[b,f]-1,4-oxazepine as an off-white solid; mp (succinic acid salt) 92°-94° C.; Rf(25% acetone/hexanes): 0.45; HRMS (FAB): MH+ of C27H24N3O3Cl, calculated 474.1584, found 474.1595.

Workup

  1. customThe product was absorbed onto silica gel
  2. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-8223378e786c43c09c86061abaf55094
Source dataset
uspto-grants-1997_12
Patent number
US05703072

Reaction notes

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