Diisopropylethylamine → N,N'-bis-Cbz-2(S)-hydroxy-4-guanidino-butyric acid

HRID 1949615Notes

Reaction equation

C1[C@H](N)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2N)[C@H]([O:20][C@@H:21]2[O:25][C@H:24](CO)[C@@H:23](O[C@H]3O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@H:22]2[OH:40])[C@@H](O)[C@@H]1N.OS(O)(=O)=O.[CH2:48]([O:55][C:56]([NH:58][C:59]([N:71]1C=CC=N1)=[N:60][C:61]([O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)=[O:62])=[O:57])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:56]([N:58]([CH2:24][CH2:23][C@H:22]([OH:40])[C:21]([OH:25])=[O:20])[C:59]([NH2:71])=[N:60][C:61]([O:63][CH2:64][C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=1)=[O:62])([O:55][CH2:48][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)=[O:57]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirring solution of 2(S)-hydroxy-4-amino-butyric acid (1, 0.059 g, 0.50 mmol) in DMF (2 ml) was added N,N′-bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine (0.26 g, 0.70 mmol) followed by DIPEA (0.87 mL, 4.99 mmol) and the reaction was heated to 80° C. and stirred overnight. The crude mixture was purified on a 2-inch reverse-phase HPLC column to yield N,N′-bis-Cbz-2(S)-hydroxy-4-guanidino-butyric acid (2): MS: m/z (M+H)+ calc. 430.15, obs. 430.1.

Workup

customThe crude mixture was purified on a 2-inch reverse-phase HPLC column

Sources & evidence

ORD record: ord-7511fdd707fb47da82c9e26ac6e0aac7
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399419B2

Reaction notes

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