Hydrochloric Acid → HCID 178478820, compound

HRID 399517Notes

Reaction equation

HRID 399517 reaction equation
C([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:14]([NH2:23])=[N:15]C(OC(C)(C)C)=O)[CH2:9][N:8]1C(OC(C)(C)C)=O)(C)(C)C.[ClH:39]>O1CCOCC1>[ClH:39].[ClH:39].[NH:13]([CH2:12][C@@H:10]1[CH2:9][NH:8][C@H:7]([C:6]([OH:38])=[O:5])[CH2:11]1)[C:14]([NH2:23])=[NH:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86753215HCID 86753215, compound

Product 1

HCID 178478820HCID 178478820, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(4S)-1-(tert-Butyloxycarbonyl)-4-[N,N'-bis(tert-butyloxycarbonyl)guanidinomethyl]-L-proline tert-butyl ester (81 mg, 0.149 mmol) was treated with 4N HCl in dioxane (1 mL) at room temperature overnight. 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 38.7 mg (100%). Mass spectrum: m/z 187 (M+1); 400 MHz 1H NMR (CD3OD): δ1.85 (m, 1H); 2.61-2.80 (m, 2H); 3.13 (dd, 1H); 3.58 (dd, 1H); 4.47 (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-49c5776d023d4b7991e0494f8fce1806
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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