Dichloromethane → HCID 86709131, compound

HRID 931461Notes

Reaction equation

HRID 931461 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]([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(=O)OC(C)(C)C)=[CH:29][CH:28]=1)(=[O:26])=[O:25].C(Cl)Cl>FC(F)(F)C(O)=O>[NH2:54][CH2:53][CH2:52][O:51][CH2:50][CH2:49][O:48][CH2:47][CH2:46][O:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][O:39][CH2:38][CH2:37][O:36][CH2:35][CH2:34][CH2:33][C:30]1[CH:31]=[CH:32][C:27]([S:24]([CH2:23][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([C:13]([NH:15][CH2:16][C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)=[O:14])=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])(=[O:25])=[O:26])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 86709129HCID 86709129, compound

Product 1

HCID 86709131HCID 86709131, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
20 °C

Procedure

A solution of carbamate 60 (85 mg, 0.098 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 amine 61 (56 mg, 75%) as a white gum: 1H NMR δ 9.22 (t, J=5.8 Hz, 1H, CONH), 8.56 (d, J=1.7 Hz, 1H, H-2′), 8.46 (dd, J=4.8, 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=7.8, 4.8, 0.6 Hz, 1H, H-5′), 4.65 (s, 2H, CH2SO2), 4.51 (d, J=5.8 Hz, 2H, CH2NH), 3.49-3.50 (m, 20H, CH2O), 3.43-3.45 (m, 2H, CH2O), 3.33-3.36 (m, 2H, CH2O), 2.72 (t, J=7.3 Hz, 2H, H-r), 2.64 (t, J=5.6 Hz, 2H, H-21′″), 2.12 (s, 3H, CH3), 1.79 (br q, J=7.2 Hz, 2H, H-2′″), NH2 not observed; 13C NMR δ 165.4, 157.9, 149.8, 148.8, 148.5, 148.0, 135.7, 135.3, 135.1, 134.8, 129.1 (2), 128.7, 128.3 (2), 128.0 (2), 125.9, 125.3 (2), 123.4, 72.6, 69.7 (7), 69.6, 69.5, 69.4, 68.9, 52.8, 41.1, 40.4, 31.4, 30.4, 9.5; HRMS calcd for C39H53N4O10S (MH+): m/z 769.3477. found m/z 769.3492.

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-5da9ab8d425f40c8b6793a4fe501f8bc
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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