Dichloromethane → HCID 90295582, compound

HRID 1050220Notes

Reaction equation

HRID 1050220 reaction equation
[O:1]([CH2:9][C@H:10]1[C@H:18]2[N:13]([C:14]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][C@@H:26]([O:29][Si:30]([C:43]([CH3:46])([CH3:45])[CH3:44])([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)[C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH2:25][C:24]4=[O:47])=[CH:19][C:15]=3[O:16][CH2:17]2)[C:12](=[O:48])[O:11]1)[Si](C(C)(C)C)(C)C.B(Cl)(Cl)Cl.ClCCl>C1COCC1>[O:29]([C@@H:26]1[CH2:27][CH2:28][N:23]([C:20]2[CH:21]=[CH:22][C:14]3[N:13]4[C:12](=[O:48])[O:11][C@@H:10]([CH2:9][OH:1])[C@@H:18]4[CH2:17][O:16][C:15]=3[CH:19]=2)[C:24](=[O:47])[CH2:25]1)[Si:30]([C:43]([CH3:45])([CH3:44])[CH3:46])([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 90295581HCID 90295581, compound

Product 1

HCID 90295582HCID 90295582, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound (3R,3 aS)-3-((t-butyldimethylsiloxy)methyl)-7-((R)-4-(t-butyldiphenylsiloxy)-2-oxopiperidin-1-yl)-3a,4-dihydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-1(3H)-one (0.78 g, 1.135 mmol) was dissolved in THF. A solution of BCl3 in dichloromethane (1M, 6.81 ml, 6.81 mmol) was added, stirred at room temperature for 24 h, and dried by spinning. Column chromatography afforded pale yellow solid 0.56 g, yield 86.0%.

Workup

  1. customdried

Sources & evidence

ORD record
ord-8f3a7a52860044d28daba16b949062d9
Source dataset
uspto-grants-2016_07
Patent number
US09382265B2

Reaction notes

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