Triethylamine → (4-phenylphenyl)-methyl-N-[(2R*,3R*)-2-isopropyl-4-oxo-oxetan-3-yl]-carbamate

HRID 530561Notes

Reaction equation

HRID 530561 reaction equation
O[C@H](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:28]([CH:50]([CH3:52])[CH3:51])[C@@H:29]([N:33]([C:38]1C=CC(C2C=CC=CC=2)=CC=1)[C:34]([O:36]C)=[O:35])[C:30]([OH:32])=[O:31].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:36][C:34](=[O:35])[N:33]([CH3:38])[C@H:29]3[C:30](=[O:32])[O:31][C@@H:28]3[CH:50]([CH3:52])[CH3:51])=[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 86700003(2R*,3S*)-3-hydroxy-4-methyl-2-[(4-phenylphenyl)-methoxy-carbonylamino]-pentanoic acidHCID 86700005(2R*,3R*)-3-hydroxy-4-methyl-2-[(4-phenylphenyl)-methoxy-carbonylamino]-pentanoic acid

Product 1

HCID 86700004(4-phenylphenyl)-methyl-N-[(2R*,3R*)-2-isopropyl-4-oxo-oxetan-3-yl]-carbamateYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, to a stirred mixture of (2R*,3R*)-3-hydroxy-4-methyl-2-[(4-phenylphenyl)-methoxy-carbonylamino]-pentanoic acid and (2R*,3S*)-3-hydroxy-4-methyl-2-[(4-phenylphenyl)-methoxy-carbonylamino]-pentanoic acid (0.059 g, 0.17 mmol) in dry CH2Cl2 (7.0 mL), at 0° C., Et3N (0.07 mL, 0.5 mmol) and subsequently TBTU (0.065 g, 0.2 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 (0.01 g, 17%), as pure anti diastereoisomer, as white solid. MS (ESI) m/z: 357 [M−NH4]+; (ESI) m/z: 338 [M−H]−. 1H NMR (DMSO-d6) δ 0.89 (d, J=6.79 Hz, 3H), 0.97 (d, J=6.57 Hz, 3H), 1.81-2.12 (m, 1H), 4.26 (dd, J=4.38, 9.11 Hz, 1H), 4.80 (dd, J=4.39, 8.16 Hz, 1H), 5.12 (s, 2H), 7.29-7.54 (m, 5H), 7.63-7.77 (m, 4H), 8.26 (d, J=8.21 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-df59dc5ddb564a8a817c8c6d24b5f5b1
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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