HCID 178454231, compound → HCID 178511838, compound
Reaction equation
C(OC(N[C@@H]([C@H]1CC[C@H](O)CC1)C(OC)=O)=O)(C)(C)C.[OH:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([C@H:28]([NH:36]C(=O)OC(C)(C)C)[C:29](=[O:35])[N:30]2[CH2:34][CH2:33][S:32][CH2:31]2)[CH2:24][CH2:23]1>>[NH2:36][C@@H:28]([C@H:25]1[CH2:26][CH2:27][C@H:22]([OH:21])[CH2:23][CH2:24]1)[C:29](=[O:35])[N:30]1[CH2:34][CH2:33][S:32][CH2:31]1Participants
Procedure
3.5 g (12.2 mmol) of methyl trans-(2S)-[(tert-butoxycarbonyl)-amino](4-hydroxycyclohexyl)-ethanoate was converted to 3.34 g of tert-butyl trans-(1S)-1-(4-hydroxycyclohexyl)-2-oxo-2-(1,3-thiazolidin-3-yl)ethyl-carbamate using the procedures outlined in Example 1, Step C. 1H NMR (400 MHz, CD3OD, mixture of rotamers) δ 4.65–4.47 (m, 1.5H), 4.19–4.05 (m, 1.5H), 3.55–3.40 (m, 1H), 3.17–3.03 (m, 2H), 2.00–1.83 (m, 3H), 1.70–1.58 (m, 2H), 1.45–1.38 (m, 9H), 1.30–1.08 (m, 4H). A portion of this material was deprotected as described in Example 1, Step D to give the title compound. 1H NMR (400 MHz, CD3OD, mixture of rotamers) δ 4.65–4.63 (m, 0.5H), 4.61–4.57 (m, 1H), 4.50–4.44 (m, 0.5H), 3.93–3.85 (m, 0.5H), 3.82–3.71 (m, 1.5H), 3.50–3.38 (m, 2H), 3.15–3.02 (m, 2H), 2.01–1.83 (m, 3H), 1.63–1.59 (m, 1H), 1.55–1.45 (m, 1H), 1.30–1.05 (m, 4H).
Sources & evidence
- ORD record
- ord-535d69c15acd4a789b724b31b7e3b18b
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07026316B2
Reaction notes
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