tert-Butanol → HCID 178458570, compound

HRID 478600Notes

Reaction equation

Cl[C:2]1[C:11]2[C:10](=[O:12])[N:9]=[C:8]([C:13]3[CH:14]=[C:15]([S:23]([N:26]4[CH2:31][CH2:30][N:29]([CH2:32][CH3:33])[CH2:28][CH2:27]4)(=[O:25])=[O:24])[CH:16]=[CH:17][C:18]=3[O:19][CH2:20][CH2:21][CH3:22])[NH:7][C:6]=2[C:5]2=[CH:34][N:35]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)[N:36]=[C:4]2[N:3]=1.[OH:46]C(C)(C)C>>[OH:46][C:2]1[C:11]2[C:10](=[O:12])[N:9]=[C:8]([C:13]3[CH:14]=[C:15]([S:23]([N:26]4[CH2:31][CH2:30][N:29]([CH2:32][CH3:33])[CH2:28][CH2:27]4)(=[O:25])=[O:24])[CH:16]=[CH:17][C:18]=3[O:19][CH2:20][CH2:21][CH3:22])[NH:7][C:6]=2[C:5]2=[CH:34][N:35]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)[N:36]=[C:4]2[N:3]=1

Participants

Reactant 2

HCID 6386tert-Butanol

HCID 178458569HCID 178458569, compound

Product 1

HCID 178458570HCID 178458570, compound

Conditions

Temperature: 95 °C

Procedure

To the uncyclized intermediate from example 3 (30 mg) under nitrogen was added K—OtBu (1M, 0.05 mL) and HOtBu (2 mL). The mixture was then heated at 95° C. for 1 h. After cooling to rt, the mixture was subjected to preparative HPLC to give the titled compound (4.5 mg). LC: 3.54′ (Gradient 1); MH+: 634.

Workup

temperatureAfter cooling to rt

Sources & evidence

ORD record: ord-dc6074beec6c46e396a3e0b1bd45ecdf
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642244B2

Reaction notes

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