HCID 90060183, compound → HCID 90060253, compound

HRID 1779208Notes

Reaction equation

[C:1]([Si:5]([CH3:60])([CH3:59])[O:6][CH2:7][CH2:8][C@:9]([OH:58])([C@@H:17]([C:38](=[O:57])[NH:39][C@H:40]([C:53](OC)=[O:54])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]#[C:51][CH3:52])=[CH:44][CH:43]=1)/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:30][CH2:29][CH2:28][O:27]1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].Cl.N[C@@H](CC1C=CC(OCC#CC)=CC=1)CO.C(OC1C=CC(C[C@H](NC([C@@H](/C=C/CCCCCCC(=O)CCCCCCC)[C@@](O)(CCO)C(OC(C)(C)C)=O)=O)C(OC)=O)=CC=1)C#CC>>[C:1]([Si:5]([CH3:60])([CH3:59])[O:6][CH2:7][CH2:8][C@:9]([OH:58])([C@@H:17]([C:38](=[O:57])[NH:39][C@H:40]([CH2:53][OH:54])[CH2:41][C:42]1[CH:43]=[CH:44][C:45]([O:48][CH2:49][C:50]#[C:51][CH3:52])=[CH:46][CH:47]=1)/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:30][CH2:29][CH2:28][O:27]1)[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 3

HCID 90060183HCID 90060183, compound

HCID 118157951HCID 118157951, compound

HCID 123758623HCID 123758623, compound

Product 1

HCID 90060253HCID 90060253, compound

Procedure

An intermediate, tert-butyl (E)-(2S,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-hydroxymethyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-undec-4-enoate (ESI (LC/MS positive mode) m/z 831 (M+H); Rt 3.98 min.) was synthesized by the synthetic method similar to that of No. 5327507, tert-butyl (E)-(2S,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-undec-4-enoate, except that (S)-2-amino-3-(4-but-2-ynyloxy-phenyl)-propan-1-ol hydrochloride was used instead of methyl (S)-2-amino-3-(4-but-2-ynyloxy-phenyl)-propionate hydrochloride. From the obtained intermediate, No. 6801976 (ESI (LC/MS positive mode) m/z 672 (M+H); Rt 2.70 min.) was synthesized by a synthetic method similar to that of No. 5217614, tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate.

Workup

custom6801976 (ESI (LC/MS positive mode) m/z 672 (M+H); Rt 2.70 min.) was synthesized by a synthetic method similar to that of No

Sources & evidence

ORD record: ord-8c9d204809944ecc85cdd0d69b37c2ca
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266853B2

Reaction notes

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