HCID 66649526, compound → HCID 131729369, compound

HRID 420290Notes

Reaction equation

C(OC([N:8]1[C@@H:16]2[C@H:11]([C@H:12]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])=[C:21]([F:36])[CH:20]=3)[CH2:13][S@:14](=[O:17])[CH2:15]2)[O:10]C1(C)C)=O)(C)(C)C>C(Cl)Cl>[CH2:29]([O:28][C:26](=[O:27])[NH:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][C@H:12]2[C@H:11]([OH:10])[C@@H:16]([NH2:8])[CH2:15][S@@:14](=[O:17])[CH2:13]2)=[CH:20][C:21]=1[F:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (3aR,5S,7S,7aS)-7-(4-benzyloxycarbonylamino-3-fluoro-benzyl)-2,2-dimethyl-5-oxo-hexahydro-1-oxa-5lambda*4*-thia-3-aza-indene-3-carboxylic acid tert-butyl ester (11.0 g, 20.1 mmol) in CH2Cl2 (80 mL) was slowly added under cooling TFA (15.5 mL, 201 mmol) and the reaction mixture was stirred for 3 h at 25° C. The reaction mixture was evaporated to dryness and the dried residue was titurated with diisopropylether. The title compound was obtained after filtration and drying as a light yellow solid: UPLC RtD=1.077 min; RtE=0.990 min; ESIMS [M+H]+=407; 1H NMR (400 MHz, CD3OD): δ 7.76 (m, 1H), 7.35 (m, 5H), 7.05 (m, 2H), 5.19 (s, 2H), 3.64 (dt, 1H), 3.41 (t, 1H), 3.34 (m, 1H), 3.25 (m, 2H), 2.82 (t, 1H), 2.57 (m, 2H), 2.01 (m, 1H).

Workup

customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record: ord-3473bd6c7d0f49a594b066d0e82ca1e6
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093406B2

Reaction notes

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