Triphenylphosphine → tert-butyl (3S)-3-({[(1aR,5S,8S,10R,22aR)-5-tert-butyl-8-{[(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]carbamoyl}-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinolin-17-yl]oxy}methyl)pyrrolidine-1-carboxylate

HRID 522398Notes

Reaction equation

HRID 522398 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[C:15]([C@H:19]1[C:46](=[O:47])[N:45]2[CH2:48][C@@H:42]([CH2:43][C@H:44]2[C:49]([NH:51][C@:52]2([C:57](=[O:66])[NH:58][S:59]([C:62]3([CH3:65])[CH2:64][CH2:63]3)(=[O:61])=[O:60])[CH2:54][C@H:53]2[CH:55]=[CH2:56])=[O:50])[O:41][C:31]2=[N:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=3[C:39](O)=[C:30]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]2[CH2:67][C@H:23]2[O:22][C:21](=[O:68])[NH:20]1)([CH3:18])([CH3:17])[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[C:15]([C@H:19]1[C:46](=[O:47])[N:45]2[CH2:48][C@@H:42]([CH2:43][C@H:44]2[C:49](=[O:50])[NH:51][C@:52]2([C:57](=[O:66])[NH:58][S:59]([C:62]3([CH3:65])[CH2:63][CH2:64]3)(=[O:60])=[O:61])[CH2:54][C@H:53]2[CH:55]=[CH2:56])[O:41][C:31]2=[N:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=3[C:39]([O:1][CH2:2][C@H:3]3[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]3)=[C:30]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]2[CH2:67][C@H:23]2[O:22][C:21](=[O:68])[NH:20]1)([CH3:16])([CH3:17])[CH3:18]

Participants

4

Reactant 3

HCID 11776TriphenylphosphineHCID 1514341tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 178455699HCID 178455699, compound

Product 1

HCID 117598995tert-butyl (3S)-3-({[(1aR,5S,8S,10R,22aR)-5-tert-butyl-8-{[(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]carbamoyl}-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinolin-17-yl]oxy}methyl)pyrrolidine-1-carboxylate

Procedure

The title compound was prepared using the same method as described in Example 75, using the tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate and (1aR,5S,8S,10R,22aR)-5-tert-butyl-N-[(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]-17-hydroxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-8-carboxamide (Example 120). The method was slightly modified as triphenylphosphine was used instead of trimethylphosphine and the reaction was done at a 0.3 M concentration LRMS (ES+) m/z 949.5 (M+H)+.

Workup

  1. concentrationthe reaction was done at a 0.3 M concentration LRMS (ES+) m/z 949.5 (M+H)+

Sources & evidence

ORD record
ord-38a3955f2d0d4ee8adc059c32ac5aa5c
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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