HCID 86709130, compound → HCID 86709129, compound

HRID 931460Notes

Reaction equation

HRID 931460 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([NH:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[O:14])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([C:33]#[C:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[CH:29][CH:28]=1)(=[O:26])=[O:25]>CO.[Pd]>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([NH:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[O:14])=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][NH:54][C:55](=[O:61])[O:56][C:57]([CH3:59])([CH3:58])[CH3:60])=[CH:29][CH:28]=1)(=[O:26])=[O:25]

Participants

4

Reactant 1

HCID 86709130HCID 86709130, compound

Product 1

HCID 86709129HCID 86709129, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of alkyne 59 (100 mg, 0.11 mmol) and 10% Pd/C (50 mg, 0.04 mmol) in MeOH (15 mL) was stirred at 20° C. under H2 (60 psi) for 2.5 h. The mixture was filtered through Celite®, washed with MeOH (100 mL), the solvent was evaporated and the residue was dried to give the carbamate 60 (85 mg, 85%) as a white gum, which was used in the next step without further purification: 1H NMR δ 9.22 (t, J=5.8 Hz, 1H, CONH), 8.57 (d, J=1.8 Hz, 1H, H-2′), 8.46 (dd, J=4.7, 1.6 Hz, 1H, H-6′), 7.99 (br d, J=8.6 Hz, 2H, H-2, H-6), 7.89 (br d, J=8.6 Hz, 2H, H-3, H-5), 7.73 (dt, J=7.9 1.9 Hz, 1H, H-4′), 7.68 (br d, J=8.3 Hz, 2H, H-2″, H-6″), 7.44 (br d, J=8.3 Hz, 2H, H-3″, H-5″), 7.36 (ddd, J=7.9, 4.8, 0.6 Hz, 1H, H-5′), 6.73 (t, J=5.5 Hz, 1H, NHCO2), 4.64 (s, 2H, CH2SO2), 4.51 (d, J=5.8 Hz, 2H, CH2NH), 3.43-3.50 (m, 20H, CH2O), 3.36 (br t, J=6.3 Hz, 4H, H-3′″, H-20′″), 3.05 (br q, J=5.9 Hz, 2H, H-21′″), 2.71 (br t, J=7.6 Hz, 2H, H-r), 2.12 (s, 3H, CH3), 1.79 (br q, J=7.1 Hz, 2H, H-2′″), 1.36 [s, 9H, (CH3)3].

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashed with MeOH (100 mL)
  3. customthe solvent was evaporated
  4. customthe residue was dried

Sources & evidence

ORD record
ord-b45e4c5d3da545c0ba29905db21fa4cb
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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