3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → HCID 86727484, compound

HRID 519107Notes

Reaction equation

HRID 519107 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:12][CH2:11][C:10]1[N:5]2[CH:6]([CH3:33])[C:7](=[O:32])[N:8](COCC[Si](C)(C)C)[N:9]=1.O=[C:35]1[CH2:38][N:37]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:36]1.C([BH3-])#N.[Na+]>CO.CC(O)=O>[C:42]([O:41][C:39]([N:37]1[CH2:38][CH:35]([NH:1][C:2]2[CH:3]=[C:4]3[C:13](=[CH:14][C:15]=2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:12][CH2:11][C:10]2[N:5]3[CH:6]([CH3:33])[C:7](=[O:32])[NH:8][N:9]=2)[CH2:36]1)=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

6

Reactant 3

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 5003444Sodium cyanoborohydrideHCID 86727485HCID 86727485, compound

Product 1

HCID 86727484HCID 86727484, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 6-amino-7-benzyloxy-4-methyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.065 g, 0.19 mmol) and tert-butyl 3-oxoazetidine-1-carboxylate (0.061 g, 0.36 mmol) in MeOH (10 mL) and AcOH (1 mL) was heated at 70° C. for 14 h. The reaction mixture was cooled to ambient temperature and sodium cyanoborohydride (0.022 g, 0.36 mmol) was added. The reaction mixture was heated at 70° C. for 1 hr then cooled to ambient temperature. The solvent was removed in vacuo and the residue was purified by preparative TLC (eluting with 50% EtOAc in petroleum ether) to give 3-(7-benzyloxy-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (0.028 g, 32%). LC/MS (Table 1, Method 2) Rt=1.205 min; MS m/z: 516 [M+23]+

Workup

  1. temperatureThe reaction mixture was heated at 70° C. for 1 hr
  2. temperaturethen cooled to ambient temperature
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by preparative TLC (eluting with 50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-f9bb2db84e2e4427b9ea7817594990e0
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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