Dichloromethane → HCID 89855225, compound

HRID 931462Notes

Reaction equation

HRID 931462 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]([CH3:61])=[C:20]([CH2:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][NH:53]C(=O)OC(C)(C)C)=[CH:28][CH:27]=3)(=[O:25])=[O:24])[N:21]=2)=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl>FC(F)(F)C(O)=O>[NH2:53][CH2:52][CH2:51][O:50][CH2:49][CH2:48][O:47][CH2:46][CH2:45][O:44][CH2:43][CH2:42][O:41][CH2:40][CH2:39][O:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33][CH2:32][C:29]1[CH:30]=[CH:31][C:26]([S:23]([CH2:22][C:20]2[N:21]=[C:17]([C:14]3[CH:13]=[CH:12][C:11]([C:9]([NH:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])=[CH:16][CH:15]=3)[O:18][C:19]=2[CH3:61])(=[O:24])=[O:25])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 131735172HCID 131735172, compound

Product 1

HCID 89855225HCID 89855225, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
20 °C

Procedure

A solution of carbamate 62 (55 mg, 0.064 mmol) in a mixture of trifluoroacetic acid (2 mL) and anhydrous DCM (8 mL) was stirred at 20° C. for 1 h. The solvent was evaporated and the residue was purified by column chromatography, eluting with 10% MeOH/DCM containing 1% aqueous NH3, to give the amine 63 (38 mg, 78%) as a white gum: 1H NMR δ 9.18 (t, J=5.9 Hz, 1H, CONH), 8.01 (br d, J=8.6 Hz, 2H, H-2, H-6), 7.89 (br d, J=8.6 Hz, 2H, H-3, H-5), 7.79 (br d, J=8.5 Hz, 2H, H-2″, H-6″), 7.68 (br d, J=8.5 Hz, 2H, H-3″, H-5″), 7.33-7.34 (m, 4H, H-2′, H-3′, H-5′, H-6′), 7.22-7.28 (m, 1H, H-4′), 4.74 (s, 2H, CH2SO2), 4.49 (d, J=5.9 Hz, 2H, CH2NH), 4.45 (s, 2H, CH2C≡C), 3.62-3.65 (m, 2H, CH2O), 3.56-3.59 (m, 2H, CH2O), 3.50-3.52 (m, 16H, CH2O), 3.38 (t, J=5.7H, 2H, CH2O), 2.69 (t, J=5.5 Hz, 2H, H-21′″), 2.17 (s, 3H, CH3), NH2 not observed; 13C NMR δ 165.4, 158.1, 150.1, 139.5, 138.2, 135.7, 132.0 (2), 128.7, 128.6, 128.3 (2), 128.1 (2), 127.4, 127.2 (2), 126.8 (2), 125.7, 125.4 (2), 90.1, 84.1, 71.7, 69.8 (6), 69.7, 69.6, 69.5, 68.8, 58.0, 52.7, 42.7, 40.8, 9.7; HRMS calcd for C40H50N3O10S (MH+): m/z 764.3211. found m/z 769.3227.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography
  3. washeluting with 10% MeOH/DCM containing 1% aqueous NH3

Sources & evidence

ORD record
ord-d9dfe0388bae4e90ba30c21123d7dc8b
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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