Hexamethylphosphoramide → HCID 57248906, compound

HRID 840136Notes

Reaction equation

[O:1]=[C:2]1[CH2:7][N:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[C@@H:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:3]1.Br[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([F:47])([F:46])[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[CH:34][CH:33]=1.CN(P(N(C)C)(N(C)C)=O)C.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[CH2:11]([O:10][C:8]([N:6]1[C@@H:5]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:3][C:2](=[O:1])[C@H:7]1[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([C:38]([F:46])([F:47])[C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40])=[CH:36][CH:37]=1)=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled solution at −78° C. of benzyl (2R, 3S)-(−)-6 oxo-2,3 diphenyl-4 morpholine carboxylate (10.5 g) and tert butyl 2-{4-(bromomethyl)phenyl}-2,2-difluoroacetate (6.2 g) and HMPA 55 mL in THF 550 ml. was added LiHMDS (28 mL, 1 M in THF) over a period of 1 hour 20 minutes. The reaction mixture was stirred further at −78° C. for 1 hour.

Workup

customat −78° C.

Sources & evidence

ORD record: ord-06b578b388fc4c0abfa30e65cf0af7db
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365592B1

Reaction notes

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