Triethylamine → (4-phenyl-phenyl)-methyl-N-[(2R*,3R*)-2-tert-butyl-4-oxo-oxetan-3-yl]-carbamate

HRID 530574Notes

Reaction equation

HRID 530574 reaction equation
O[C@H](C(C)(C)C)[C@@H](N([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)C(OC)=O)C(O)=O.O[C@@H:29]([C:51]([CH3:54])([CH3:53])[CH3:52])[C@@H:30]([N:34]([C:39]1C=CC(C2C=CC=CC=2)=CC=1)[C:35]([O:37]C)=[O:36])[C:31]([OH:33])=[O:32].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[C:18]1([C:15]2[CH:14]=[CH:13][C:12]([O:37][C:35](=[O:36])[N:34]([CH3:39])[C@H:30]3[C:31](=[O:33])[O:32][C@@H:29]3[C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:17][CH:16]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86700023(2R*,3S*)-3-hydroxy-4,4-dimethyl-2-[(4-phenyl-phenyl)-methoxy-carbonylamino]-pentanoic acidHCID 86700025(2R*,3R*)-3-hydroxy-4,4-dimethyl-2-[(4-phenyl-phenyl)-methoxy-carbonylamino]-pentanoic acid

Product 1

HCID 86700024(4-phenyl-phenyl)-methyl-N-[(2R*,3R*)-2-tert-butyl-4-oxo-oxetan-3-yl]-carbamateYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, to a stirred mixture of (2R*,3R*)-3-hydroxy-4,4-dimethyl-2-[(4-phenyl-phenyl)-methoxy-carbonylamino]-pentanoic acid and (2R*,3S*)-3-hydroxy-4,4-dimethyl-2-[(4-phenyl-phenyl)-methoxy-carbonylamino]-pentanoic acid (0.203 g, 0.55 mmol) in dry CH2Cl2 (25 mL), at 0° C., Et3N (0.23 mL, 1.65 mmol) and subsequently TBTU (0.21 g, 0.66 mmol) were added. The mixture was left stirring at 0° C. for 1 h and at rt for 15 h. The organics were then removed under reduced pressure, and the resulting crude product purified by column chromatography, using a Teledyne ISCO apparatus, eluting with Cy:AcOEt (from 90:10 to 80:20) to afford the pure title compound (0.063 g, 58%), as pure anti diastereoisomer, as white solid. MS (ESI) m/z: 371 [M−NH4]+; (ESI) m/z: 352 [M−H]−. 1H NMR (DMSO-d6) δ 0.95 (s, 9H), 4.37 (d, J=4.64 Hz, 1H), 4.83 (dd, J=4.65, 8.16 Hz, 1H), 5.14 (s, 2H), 7.32-7.56 (m, 5H), 7.60-7.75 (m, 4H), 8.25 (d, J=8.12 Hz, 1H).

Workup

  1. waitThe mixture was left
  2. customThe organics were then removed under reduced pressure
  3. customthe resulting crude product purified by column chromatography
  4. washeluting with Cy

Sources & evidence

ORD record
ord-9461816081604c799311e4a12921e17e
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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