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HCID 69083734, compound → HCID 69280781, compound

HRID 1396248
Notes
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Reaction equation

HRID 1396248 reaction equation
[Li][CH2:2]CCC.[CH:6]([C@H:8]1[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[S:14]2)[C@@H:10]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[C@@H:9]1[O:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)=O.OC[C@H]1O[C@H]2[C@H](N=C(N(C)C(=O)OC(C)(C)C)S2)[C@@H](OCC2C=CC(OC)=CC=2)[C@@H]1OCC1C=CC(OC)=CC=1.CN(C)C1S[C@H]2O[C@H](CO)[C@@H](OCC3C=CC(OC)=CC=3)[C@H](OCC3C=CC(OC)=CC=3)[C@H]2N=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH3:45][O:44][C:41]1[CH:42]=[CH:43][C:38]([CH2:37][O:36][C@@H:9]2[C@@H:8]([CH:6]=[CH2:2])[O:16][C@H:15]3[C@H:11]([N:12]=[C:13]([N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[S:14]3)[C@H:10]2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[CH:39][CH:40]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 69083734HCID 69083734, compoundHCID 69280765HCID 69280765, compoundHCID 86701105HCID 86701105, compoundHCID 178418339Butyllithium

Product 1

HCID 69280781HCID 69280781, compound

Reagents, catalysts & solvents 2

HCID 74505
Methyltriphenyliphosphonium bromide
Catalyst
HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of methyltriphenylphosphonium bromide (1.85 g, 5.18 mmol) in tetrahydrofuran (35 mL) was treated with n-BuLi (1.9 ml, 2.5M) for 30 min at 0° C., and followed by addition of tert-butyl (3aR,5S,6S,7R,7aR)-5-formyl-6,7-bis(4-methoxybenzyloxy)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(methyl)carbamate (44) prepared from compound 28 by a procedure identical to that described for the conversion of 10 to 11) (0.6 g, 1.05 mmol) in THF (5 mL). The resulting solution was stirred overnight at room temperature, quenched by water (25 mL), and extracted with dichloromethane (3×25 ml). The combined organic layers were dried over magnesium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 20% ethyl acetate in petroleum ether to give crude compound 45 as a yellow oil (220 mg, purity 50% by LC-MS). (ES, m/z): [M+H]+ 571.0.

Workup

  1. customquenched by water (25 mL)
  2. extractionextracted with dichloromethane (3×25 ml)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give a residue, which
  6. customwas purified by a silica gel column
  7. washeluted with 20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-2edf49bb4f0344a48b514003264fa21d
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08901087B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes