Hydrochloric Acid → HCID 11259967, compound

HRID 1270980Notes

Reaction equation

HRID 1270980 reaction equation
C(OC(=O)[N:10]([CH2:18][CH2:19][CH2:20][C@@H:21]([NH:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:35][CH:34]=1)=[O:31])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)C1C=CC=CC=1.C(OC(=O)N(CCC[C@@H](NC(OC(C)(C)C)=O)CC1C=CC=CC=1)CCN1CCCC1)C1C=CC=CC=1.Cl>C(Cl)Cl.O1CCOCC1>[CH2:22]([C@H:21]([NH:29][C:30]([NH:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[CH:37][CH:38]=1)=[O:31])[CH2:20][CH2:19][CH2:18][NH:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 69432868HCID 69432868, compoundHCID 69432902HCID 69432902, compound

Product 1

HCID 11259967HCID 11259967, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

[(R)-4-(3-Biphenyl-4-yl-ureido)-5-phenyl-pentyl]-(2-pyrrolidin-1-yl-ethyl)-carbamic acid benzyl ester. To a solution of ((R)-4-tert-butoxycarbonylamino-5-phenyl-pentyl)-(2-pyrrolidin-1-yl-ethyl)-carbamic acid benzyl ester (0.06 g, 0.16 mmol) in CH2Cl2 (1.7 mL) was added HCl in dioxane (3 M, 0.6 mL), and the solution was stirred (25° C., 1 h). The solution was concentrated in vacuo, and the residue was dissolved in MeOH (2 mL) and treated with basic resin, and the resulting suspension was stirred (25° C., 1 h). The suspension was filtered and concentrated in vacuo, and the residue was dissolved in CH2Cl2 (2.0 mL). The solution was treated with 4-biphenylisocyanate (0.033 g, 0.17 mmol), and the reaction mixture was stirred for 4 h (25° C.), during which time a precipitate, the desired product, formed. The product was collected as a clear semi-solid (0.064 g, 64%). MS (electrospray): mass calculated for C38H44N4O3, 604.79; m/z found, 605.3 [M+H]+, 627.3 [M+Na]+. 1H NMR (CDCl3, 400 MHz): 7.09–7.49 (m, 21H), 5.01–5.04 (m, 2H), 3.41 (br s, 1H), 3.14–3.30 (m, 2H), 2.85–2.92 (m, 2H), 2.49–2.58 (m, 8H), 1.17–1.56 (m, 8H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in MeOH (2 mL)
  3. additiontreated with basic resin
  4. stirringthe resulting suspension was stirred (25° C., 1 h)
  5. filtrationThe suspension was filtered
  6. concentrationconcentrated in vacuo
  7. dissolutionthe residue was dissolved in CH2Cl2 (2.0 mL)
  8. additionThe solution was treated with 4-biphenylisocyanate (0.033 g, 0.17 mmol)
  9. stirringthe reaction mixture was stirred for 4 h (25° C.)

Sources & evidence

ORD record
ord-635ef33ab6144270aeb15cad4e5409da
Source dataset
uspto-grants-2007_04
Patent number
US07202269B2

Reaction notes

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