Hydrochloric Acid → HCID 178478824, compound

HRID 399523Notes

Reaction equation

HRID 399523 reaction equation
C([O:5][C:6](=[O:37])[C@@H:7]1[CH2:11][C@H:10]([N:12](C(OC(C)(C)C)=O)[C:13]([NH2:22])=[N:14]C(OC(C)(C)C)=O)[CH2:9][N:8]1C(OC(C)(C)C)=O)(C)(C)C.[ClH:38]>O1CCOCC1>[ClH:38].[ClH:38].[NH:12]([C@@H:10]1[CH2:9][NH:8][C@H:7]([C:6]([OH:37])=[O:5])[CH2:11]1)[C:13]([NH2:22])=[NH:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86753218HCID 86753218, compound

Product 1

HCID 178478824HCID 178478824, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(4S)-1-(tert-Butyloxycarbonyl)-4-[N,N'-bis(tert-butyloxycarbonyl)guanidino]-L-proline tert-butyl ester (55 mg, 0.104 mmol) was treated with 4N HCl in dioxane (2 mL) for 48 hours at room temperature. The reaction mixture was evaporated under diminished pressure, coevaporated several times with diethyl ether and several times with methanol. The product was dried under high vacuum; yield 17.5 mg (98%). Mass spectrum: m/z 173 (M+1); 400 MHz 1H NMR (CD3OD): δ2.20 (m, 1H); 2.89 (m, 1H); 3.38 (dd, 1H); 3.73 (dd, 1H); 4.43 (m, 1H); 4.51 (t, 1H).

Workup

  1. customThe reaction mixture was evaporated under diminished pressure
  2. customThe product was dried under high vacuum

Sources & evidence

ORD record
ord-237a61aa048c4042a9222a4688780a35
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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