Trifluoroacetic acid → HCID 22961323, compound

HRID 2304858Notes

Reaction equation

C([N:8]([C@@H:24]([C:33]1[O:34][CH:35]=[C:36]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:37]=1)[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:9](=[O:23])[C@H:10]([NH2:22])[CH2:11][CH2:12][CH2:13][NH:14]C(OC(C)(C)C)=O)(OC(C)(C)C)=O.[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46]>>[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[NH2:22][C@H:10]([CH2:11][CH2:12][CH2:13][NH2:14])[C:9]([NH:8][C@@H:24]([C:33]1[O:34][CH:35]=[C:36]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:37]=1)[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:23]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 57117854HCID 57117854, compound

Product 1

HCID 22961323HCID 22961323, compound

Procedure

A solution of ethyl 2-[(1R)-1-[(2R)-N,N′-bis-Boc-2,5-diaminovaleramido]-3-phenylpropyl]-4-oxazole-carboxylate (67 mg) and trifluoroacetic acid (1 mL) was kept at 25° C. for 1 hr, concentrated in vacuo and coevaporated with toluene. The residue was purified further by reverse phase chromatography (20 mL Amberchrom, 0% to 50% CH3CN in 0.1% aqueous TFA over 45 min. at 2 ml/min. flow-rate) to give the desired compound (60 mg) as a white powder: 1H NMR (400 MHz, D2O) δ 1.41 (t, J=7.1 Hz, 3H), 1.80 (m, 2H), 2.02 (m, 2H), 2.39 (m, 1H), 2.46 (m, 1H), 2.80 (m, 1H), 2.87 (m, 1H), 3.10 (t, J=7.4 Hz, 2H), 4.17 (t, J=6.4 Hz, 1H), 4.43 (q, J=7.1 Hz, 2H), 5.14 (t, J=7.0 Hz, 1H), 7.32 (m, 3H), 7.41 (m, 2H), and 8.48 (s, 1H).

Workup

concentrationconcentrated in vacuo
customThe residue was purified further by reverse phase chromatography (20 mL Amberchrom, 0% to 50% CH3CN in 0.1% aqueous TFA over 45 min. at 2 ml/min. flow-rate)

Sources & evidence

ORD record: ord-3fd800838b2e436f9ffafbc2c60e32c0
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06436980B1

Reaction notes

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