Hydrochloric Acid → HCID 69939473, compound

HRID 1058327Notes

Reaction equation

HRID 1058327 reaction equation
O(C([N:8]1[CH2:39][CH2:38][CH:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@H:9]1[C:10]([N:12]1[CH2:36][CH2:35][CH2:34][C@H:13]1[C:14]([NH:16][CH2:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[CH2:25][NH:26]C(OC(C)(C)C)=O)=[O:15])=[O:11])=O)C(C)(C)C.Cl>CO.CCOCC>[C:40]1([CH:37]2[CH2:38][CH2:39][NH:8][C@@H:9]2[C:10]([N:12]2[CH2:36][CH2:35][CH2:34][C@H:13]2[C:14]([NH:16][CH2:17][C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[CH2:25][NH2:26])=[O:15])=[O:11])[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23560060HCID 23560060, compound

Product 1

HCID 69939473HCID 69939473, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of diastereomer A of 1-(tert-butoxylcarbonyl)-3-phenylprolyl-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)-L-prolinamide (60 mg, 0.09 mmol) from the previous step in approx. 2 mL MeOH at room temperature was added excess of a solution of 1.0 M HCl in ether. The reaction was monitored for completeness by LCMS. The solvent was removed in vacuo to give the HCl salt of the title compound as a white solid. LCMS RT=0.94 min. LCMS (M+H)=441.1. 1H NMR (CD3OD, 500 MHz): δ 7.50-7.23 (m, 8H), 4.58-4.51 (m, 1H), 4.41-4.24 (m, 3H), 4.08-3.96 (m, 1H), 3.80-3.74 (m, 1H), 3.49-3.43 (m, 1H), 3.39-3.31 (m, 3H), 3.05-2.92 (m, 1H), 2.57-2.37 (m, 2H), 2.06-1.64 (m, 2H), 1.56-1.26 (m, 2H). Diastereomer B (73 mg, 0.11 mmol) was deprotected in similar fashion to afford the HCl salt of the title compound as a white solid. LCMS RT=0.98 min. LCMS (M+H)=441.2. 1H NMR (CD3OD, 400 MHz): δ 8.90 (m, 1H), 7.49-7.32 (m, 8H), 4.49 (d, J=15.6 Hz, 1H), 4.31 (d, J=15.6 Hz, 1H), 4.23 (s, 2H), 4.02-3.95 (m, 1H), 3.90-3.87 (m, 1H), 3.79-3.75 (m, 1H), 3.48-3.30 (m, 2H), 3.13-3.03 (m, 1H), 2.91-2.85 (m, 1H), 2.50-2.43 (m, 1H), 2.39-2.28 (m, 1H), 1.73-1.59 (m, 3H), 1.18-1.12 (m, 1H).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-324bb4a9a8d04024a1f2541373be9c03
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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