Water → HCID 178442402, compound

HRID 1046408Notes

Reaction equation

C[O:2][C:3]([C:5]1[S:6][C:7]([C:32]#[C:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:23][C@H:22]([O:24][CH2:25][C:26]2C=CC=CC=2)[CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=O.[C:38](#[N:40])[CH3:39].F[C:42](F)(F)C(O)=O.[OH2:48]>>[CH3:36][C:34]([CH3:37])([CH3:35])[C:33]#[C:32][C:7]1[S:6][C:5]([C:3]([OH:2])=[O:48])=[C:9]([N:10]([C:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]2)=[O:12])[C@H:20]2[CH2:21][C@H:22]([O:24][C:25]3[CH:26]=[N:40][CH:38]=[CH:39][CH:42]=3)[CH2:23]2)[CH:8]=1

Participants

Reactant 4

HCID 962Water

HCID 6342Acetonitrile

HCID 6422Trifluoroacetic acid

HCID 178499349HCID 178499349, compound

Product 1

HCID 178442402HCID 178442402, compound

Procedure

The title compound was synthesized in a manner analogous to Example 20, using 3-[(trans-3-benzyloxy-cyclobutyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester in place of 3-[(cis-3-benzyloxy-cyclobutyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester: MS (m/z): 492.8 [M−H]−; HPLC retention time: 3.45 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

Sources & evidence

ORD record: ord-40c25df9c8544ea7aa048c9fe4de54db
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569302B2

Reaction notes

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