Triethylamine → 5-phenylpentyl-N-[(2R*,3R*)-2-tert-butyl-4-oxo-oxetan-3-yl]-carbamate

HRID 530572Notes

Reaction equation

HRID 530572 reaction equation
O[C@H:2]([C:22]([CH3:25])([CH3:24])[CH3:23])[C@@H:3]([NH:7][C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:9])[C:4]([OH:6])=[O:5].O[C@@H](C(C)(C)C)[C@@H](NC(OCCCCCC1C=CC=CC=1)=O)C(O)=O.CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:8](=[O:9])[NH:7][C@H:3]2[C:4](=[O:6])[O:5][C@@H:2]2[C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86700020(2R*,3S*)-3-hydroxy-4,4-dimethyl-2-(5-phenylpentoxy-carbonylamino)-pentanoic acidHCID 86700022(2R*,3R*)-3-hydroxy-4,4-dimethyl-2-(5-phenylpentoxy-carbonylamino)-pentanoic acid

Product 1

HCID 867000215-phenylpentyl-N-[(2R*,3R*)-2-tert-butyl-4-oxo-oxetan-3-yl]-carbamateYield 54%

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-(5-phenylpentoxy-carbonylamino)-pentanoic acid and (2R*,3S*)-3-hydroxy-4,4-dimethyl-2-(5-phenylpentoxy-carbonylamino)-pentanoic acid (0.325 g, 0.92 mmol) in dry CH2Cl2, (40 mL). at 0° C., Et3N (0.38 mL, 2.77 mmol) (0.2 mL, 1.44 mmol) and subsequently TBTU (0.356 g, 1.11 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 70:30) to afford the title compound (0.165 g, 54%), as pure anti diastereoisomer, as white solid. MS (ESI) m/z: 351 [M−NH4]+; (ESI) m/z: 332 [M−H]−. 1H NMR (DMSO-d6) δ 0.94 (s, 9H), 1.29-1.39 (m, 2H), 1.52-1.65 (m, 4H), 2.58 (t, J=7.65 Hz, 2H), 4.01 (t, J=6.59 Hz, 2H), 4.33 (d, J=4.66 Hz, 1H), 4.76 (dd, J=4.65, 8.16 Hz, 1H), 7.11-7.36 (m, 5H), 8.05 (d, J=8.15 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-4c5b13de1cb24bd0882f3cf1d1577115
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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