Hydrochloric Acid → HCID 66884776, compound

HRID 72137Notes

Reaction equation

HRID 72137 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:23])OC1C=CC([N+]([O-])=O)=CC=1)[CH2:8]2.[NH:24]1[CH2:27][CH:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:25]1.CCN(C(C)C)C(C)C.Cl>C(Cl)Cl>[CH:3]12[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8][CH:1]([CH2:10]3)[CH:2]1[NH:11][C:12]([N:24]1[CH2:27][CH:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:25]1)=[O:23])[CH2:9]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 15194053-Aminoazetidine, 3-BOC protectedHCID 86653266HCID 86653266, compound

Product 1

HCID 66884776HCID 66884776, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-nitrophenyl (2-adamantyl)carbamate (40 mg, 0.12 mmol) in CH2Cl2 (2 mL) was added tert-butyl azetidin-3-ylcarbamate (40 mg, 0.23 mmol), followed by i-Pr2NEt (0.05 mL, 0.28 mmol). The mixture was stirred over the weekend and applied to a 10-mL ChemElut cartridge prewetted with 5% aq HCl (6 mL). The cartridge was eluted with ether (20 mL). The eluate was evaporated to dryness and the residue was applied to 2-g silica SPE cartridge which was eluted sequentially with 0, 25, 50, 75, 100 and 100% EtOAc in hexanes (15 mL of each) to afford six fractions. Fraction 4 was concentrated to provide tert-butyl 1-(2-adamantylcarbamoyl)azetidin-3-ylcarbamate (19 mg, 43%). LC-MS Method 1, tR=1.74 min, m/z=350, 294; 1H NMR (CDCl3) 1.45 (s, 9H), 1.60-1.95 (14H), 3.75 (m, 2H), 3.89 (m, 1H), 4.22 (m, 2H), 4.39 (d, 1H), 4.46 (1H), 5.06 (1H).

Workup

  1. washThe cartridge was eluted with ether (20 mL)
  2. customThe eluate was evaporated to dryness
  3. washwas eluted sequentially with 0, 25, 50, 75, 100 and 100% EtOAc in hexanes (15 mL of each)
  4. customto afford six fractions
  5. concentrationFraction 4 was concentrated

Sources & evidence

ORD record
ord-19383af1440f4e29979df11c20162b12
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Reaction notes

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