1-Chloro-2-pentyne → (2S,3R,6S)-2,6-Dimethyl-4-(4-pent-2-ynyloxy-benzenesulfonyl)-morpholine-3-carboxylic acid methyl ester

HRID 1935345

Reaction equation

HRID 1935345 reaction equation
Cl[CH2:2][C:3]#[C:4][CH2:5][CH3:6].[CH3:7][O:8][C:9]([C@H:11]1[C@H:16]([CH3:17])[O:15][C@@H:14]([CH3:18])[CH2:13][N:12]1[S:19]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)(=[O:21])=[O:20])=[O:10]>>[CH3:7][O:8][C:9]([C@H:11]1[C@H:16]([CH3:17])[O:15][C@@H:14]([CH3:18])[CH2:13][N:12]1[S:19]([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:2][C:3]#[C:4][CH2:5][CH3:6])=[CH:26][CH:27]=1)(=[O:21])=[O:20])=[O:10]

Participants

3

Reactant 2

HCID 897641-Chloro-2-pentyneHCID 12016690(2S,3R,6S)-4-(4-Hydroxy-benzenesulfonyl)-2,6-dimethyl-morpholine-3-carboxylic acid methyl ester

Product 1

HCID 12016687(2S,3R,6S)-2,6-Dimethyl-4-(4-pent-2-ynyloxy-benzenesulfonyl)-morpholine-3-carboxylic acid methyl ester

Procedure

The title compound was prepared in a manner similar to Preparation 3 from 1-chloro-pent-2-yne and (2S,3R,6S)-4-(4-Hydroxy-benzenesulfonyl)-2,6-dimethyl-morpholine-3-carboxylic acid methyl ester. 1HNMR (400 MHz, CDCl3): δ=7.70 (d, J=8.9 Hz, 2H), 7.0 (d, J=8.9 Hz, 2H), 4.71 (bs, 2H), 4.52 (q, J=7.0 Hz, 1H), 4.27 (s, 1H), 3.97 (m, 1H), 3.54 (s, 3H), 2.98 (dd, J=12.1 and 10.8, 1H), 2.21 (m, 2H), 1.44 (d, J=6.9 Hz, 3H), 1.11 (t, J=7.5 Hz, 3H), 1.05 (d, J=6.0 Hz, 3H).

Sources & evidence

ORD record
ord-adc9652276bf4a8c9b7e73dee505412c
Source dataset
uspto-grants-2002_05
Patent number
US06387901B1

Linked notes

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