Tetrahydrofuran → HCID 87631652, compound

HRID 2400310Notes

Reaction equation

HRID 2400310 reaction equation
C([O:5][C:6](=[O:40])[C@@H:7]([NH:13][C:14](=[O:39])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:28][CH:27]=1)[CH2:8][CH2:9][C:10]([OH:12])=[O:11])(C)(C)C.CCN([CH:47]([CH3:49])[CH3:48])C(C)C.CN(C(O[N:58]1[C:63](=[O:64])[CH2:62][CH2:61][C:59]1=[O:60])=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:72]1COCC1>>[O:60]=[C:59]1[CH2:61][CH2:62][C:63](=[O:64])[N:58]1[O:5][C:6](=[O:40])[C@@H:7]([NH:13][C:14](=[O:39])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:30][CH:31]=1)[CH2:8][CH2:9][C:10]([O:12][C:47]([CH3:49])([CH3:72])[CH3:48])=[O:11]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 16211151(Dimethylamino)((2,5-dioxopyrrolidin-1-yl)oxy)-N,N-dimethylmethaniminium hexafluorophosphateHCID 68944855HCID 68944855, compound

Product 1

HCID 87631652HCID 87631652, compound

Procedure

(S)-2-[12-(4-tert-Butoxycarbonylphenyl) dodecanoylamino]pentanedioic acid 1-tert-butyl ester (158 mg, 0.28 mmol) was dissolved in THF (6 ml). DIEA (48 μl, 0.28 mmol) was added, and the solution was placed in an ice bath. HSTU (101 mg, 0.28 mmol) was added, and the solution was stirred for 16 h, warming to rt slowly. The solvent was removed under vacuum, and the residue was partitioned between AcOEt (25 ml) and 5% AcOH (15 ml). The organic phase was washed with 5% AcOH (2×15 ml), and saturated NaHCO3, dried, and concentrated under vacuum to yield an oil (0.16 g).

Workup

  1. customthe solution was placed in an ice bath
  2. customThe solvent was removed under vacuum
  3. customthe residue was partitioned between AcOEt (25 ml) and 5% AcOH (15 ml)
  4. washThe organic phase was washed with 5% AcOH (2×15 ml), and saturated NaHCO3
  5. customdried
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-23afe677a3ce404b85fdfcba67b7f367
Source dataset
uspto-grants-2014_08
Patent number
US08796205B2

Reaction notes

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