Bromotrimethylsilane → 3-(4-(2-((R)-2-amino-3-((R)-2,3-bis(dodecanoyloxy)propylthio)propanamido)ethyl)phenoxy)propylphosphonic acid

HRID 2407896ノート

反応式

HRID 2407896 の反応式
[C:1]([O:14][CH2:15][C@@H:16]([O:45][C:46](=[O:58])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:17][S:18][CH2:19][C@H:20]([NH2:44])[C:21]([NH:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][P:36]([O:41]CC)([O:38]CC)=[O:37])=[CH:28][CH:27]=1)=[O:22])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C[Si](Br)(C)C>C(Cl)Cl>[NH2:44][C@@H:20]([CH2:19][S:18][CH2:17][C@H:16]([O:45][C:46](=[O:58])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:15][O:14][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:21]([NH:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][P:36](=[O:37])([OH:41])[OH:38])=[CH:28][CH:27]=1)=[O:22]

参加物

4

反応物 2

HCID 76113BromotrimethylsilaneHCID 86678289(R)-3-((R)-2-amino-3-(4-(3-(diethoxyphosphoryl)propoxy)phenethylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate

生成物 1

HCID 534764323-(4-(2-((R)-2-amino-3-((R)-2,3-bis(dodecanoyloxy)propylthio)propanamido)ethyl)phenoxy)propylphosphonic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (R)-3-((R)-2-amino-3-(4-(3-(diethoxyphosphoryl)propoxy)phenethylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate (1 eq) in DCM (0.1 M) was added trimethylsilyl bromide (10 eq). The reaction mixture was stirred at room temperature overnight and then concentrated. The crude mixture was purified by reverse phase high performance liquid chromatography (HPLC) with C4 column eluting with a gradient of 50-100% MeCN/10 mM NH4OAc (95:5) in 10 mM NH4OAc (pH 9) to give the product as a white solid. 1H NMR (DMSO-d6): δ 7.13 (d, 2H), 6.85 (d, 2H), 5.10-5.19 (m, 2H), 4.28 (dd, 1H), 4.12 (dd, 1H), 3.97 (t, 1H), 3.81-3.90 (m, 1H), 2.93 (dd, 1H), 2.70-2.86 (m, 3H), 2.64-2.70 (m, 2H), 2.31-2.35 (m, 2H), 2.24-2.31 (m, 2H), 2.14-2.21 (m, 2H), 1.82-1.93 (m, 4H), 1.57-1.70 (m, 4H), 1.41-1.57 (m, 4H), 1.07-1.38 (m, 32H), 0.85 (t, 6H). LRMS [M+H]=801.5.

後処理

  1. concentrationconcentrated
  2. customThe crude mixture was purified by reverse phase high performance liquid chromatography (HPLC) with C4 column
  3. washeluting with a gradient of 50-100% MeCN/10 mM NH4OAc (95:5) in 10 mM NH4OAc (pH 9)

出典と根拠

ORDレコード
ord-f9723935b3ba41c79000fea30bd2d882
出典データセット
uspto-grants-2014_08
特許番号
US08808703B2

反応ノート

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