Hydrochloric Acid → HCID 54342562, compound

HRID 399520Notes

Reaction equation

HRID 399520 reaction equation
[C:1]([O:5][C:6](=[O:38])[C@@H:7]1[CH2:11][C@@H:10]([CH2:12][N:13](C(OC(C)(C)C)=O)C(N)=NC(OC(C)(C)C)=O)[CH2:9][N:8]1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.N(C[C@H]1CN[C@H](C(O)=O)C1)C(N)=N.Cl>O1CCOCC1>[C:1]([O:5][C:6](=[O:38])[C@@H:7]1[CH2:11][C@@H:10]([C:12]#[N:13])[CH2:9][N:8]1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178454314HCID 178454314, compound

Product 1

HCID 54342562HCID 54342562, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(4R)-4-(Guanidinomethyl)-L-Proline Dihydrochloride (4R)-1-(tert-Butyloxycarbonyl)-4-[N,N'-bis(tert-butyloxy-carbonyl)guanidino-methyl]-L-proline tert-butyl ester (98 mg, 0.181 mmol) was treated with 4N HCl in dioxane (1.5 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 44 mg (94%). Mass spectrum: m/z 187 (M+1); 400 MHz 1H NMR (CD3OD): δ2.19 (m, 1H); 2.43 (m, 1H); 2.68 (m, 1H); 3.11 (dd, 1H); 3.63 (dd, 1H).

Workup

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

Sources & evidence

ORD record
ord-7409d93e9c5b4c77acb0d986c4c640c5
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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