Tert-butyl 3-aminoazetidine-1-carboxylate → HCID 86727434, compound

HRID 519068Notes

Reaction equation

HRID 519068 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:12][CH2:11][C:10]1[N:5]2[CH:6]([CH3:24])[C:7](=[O:23])[NH:8][N:9]=1.N[CH:26]1[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27]1.C([BH3-])#N.[Na+]>CO.CC(O)=O>[C:33]([O:32][C:30]([N:28]1[CH2:29][CH:26]([NH:1][C:2]2[CH:3]=[C:4]3[C:13](=[CH:14][C:15]=2[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:12][CH2:11][C:10]2[N:5]3[CH:6]([CH3:24])[C:7](=[O:23])[NH:8][N:9]=2)[CH2:27]1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 3

HCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 86727433HCID 86727433, compound

Product 1

HCID 86727434HCID 86727434, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

A mixture of 6-amino-4-methyl-7-phenoxy-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.090 g, crude from previous step), tert-butyl 3-aminoazetidine-1-carboxylate (0.087 g, 0.51 mmol) and sodium cyanoborohydride (0.00032 g, 0.51 mmol) in MeOH (2.7 mL) and AcOH (0.3 mL) was heated at reflux overnight. The reaction mixture was cooled to ambient temperature and diluted with MeOH (10 mL). The solution was purified by preparative HPLC (Table 3, Method 3) to give 3-(4-methyl-3-oxo-7-phenoxy-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (0.015 g, 12% over 2 steps) as a colorless oil. LC/MS (Table 1, Method 2) Rt=1.188 min; MS m/z: 502 [M+23]+

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe solution was purified by preparative HPLC (Table 3, Method 3)

Sources & evidence

ORD record
ord-5d0da1b1d1f643c197d24d0d4a177133
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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