tert-Butanol → HCID 86594157, compound

HRID 1893121Notes

Reaction equation

HRID 1893121 reaction equation
C([O:8][P:9]([O:36][CH2:37][CH2:38][NH:39][C:40](=[O:66])[CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][CH2:48][O:49][CH2:50][CH2:51][O:52][CH2:53][CH2:54][NH:55]C(OCC1C=CC=CC=1)=O)([O:11][CH2:12][CH:13]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:14][O:15][C:16](=[O:30])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:10])C1C=CC=CC=1.CC(O)(C)C>[Pd].O>[NH2:55][CH2:54][CH2:53][O:52][CH2:51][CH2:50][O:49][CH2:48][CH2:47][O:46][CH2:45][CH2:44][O:43][CH2:42][CH2:41][C:40]([NH:39][CH2:38][CH2:37][O:36][P:9]([OH:10])([O:11][CH2:12][CH:13]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:14][O:15][C:16](=[O:30])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])=[O:8])=[O:66]

Participants

5

Reactant 2

HCID 6386tert-ButanolHCID 86594158HCID 86594158, compound

Product 1

HCID 86594157HCID 86594157, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A suspension of 9 (30.2 mg, 0.0313 mmol) and 10% Pd/C (11.3 mg) in 6:1 t-BuOH:H2O was shaken under an atmosphere of H2 (50 psi) for 5.5 hours. The reaction was filtered through a pad of Celite 545 and the pad was washed with 6:1 t-BuOH:H2O (10 mL) and EtOH (2×10 mL). The solvents were evaporated and the product was used in subsequent steps without further purification. RF=0.59 (10:5:1 CHCl3:MeOH:H2O); δH (CD3OD): 4.16 (dt, 1H), 4.05 (dd, 1H), 3.80-4.02 (m, 5H), 3.71-3.79 (m, 4H), 3.59-3.71 (m, 13H), 3.45 (m, 2H), 3.14 (t, 2H), 3.02 (t, 2H), 2.50 (t, 2H), 2.30-2.39 (m, 2H), 1.63 (quin, 2H), 1.47 (quin, 2H), 1.43 (s, 9H), 1.28-1.28 (m, 2H), 1.22 (s, 9H); δP (CD3OD): 0.28; MALDI-MS: 732.4 ((M+H)+, 100.0).

Workup

  1. filtrationThe reaction was filtered through a pad of Celite 545
  2. washthe pad was washed with 6:1 t-BuOH
  3. customThe solvents were evaporated
  4. customthe product was used in subsequent steps without further purification

Sources & evidence

ORD record
ord-fc762c94b0ea46bdbf27d5bb6af8ee87
Source dataset
uspto-grants-2013_08
Patent number
US08512971B2

Reaction notes

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