tert-Butyl isocyanate → HCID 58327073, compound

HRID 879868Notes

Reaction equation

HRID 879868 reaction equation
C[O:2][C:3](=[O:52])[C@@H:4]([NH:21][C:22]([C@@H:24]1[CH2:33][C:32]2[CH:31]=[C:30]3[O:34][CH2:35][C@H:36]([C:38]4[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH:46]5[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]5)=[CH:40][CH:39]=4)[O:37][C:29]3=[CH:28][C:27]=2[CH2:26][NH:25]1)=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[C:14]=2[CH3:20])=[CH:8][CH:7]=1.[N:53]([C:56]([CH3:59])([CH3:58])[CH3:57])=[C:54]=[O:55]>C(Cl)Cl>[C:56]([NH:53][C:54]([N:25]1[C@H:24]([C:22]([NH:21][C@@H:4]([CH2:5][C:6]2[CH:7]=[CH:8][C:9]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[C:14]=3[CH3:20])=[CH:10][CH:11]=2)[C:3]([OH:2])=[O:52])=[O:23])[CH2:33][C:32]2[CH:31]=[C:30]3[O:34][CH2:35][C@H:36]([C:38]4[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH:46]5[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]5)=[CH:40][CH:39]=4)[O:37][C:29]3=[CH:28][C:27]=2[CH2:26]1)=[O:55])([CH3:59])([CH3:58])[CH3:57]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 58327430HCID 58327430, compound

Product 1

HCID 58327073HCID 58327073, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-{[(3S,8S)-3-(4-cyclohexylmethoxy-phenyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester (25 mg) in DCM was added 2-isocyanato-2-methyl-propane (5 eq.) and the reaction stirred was at room temperature for 1 hour. The reaction mixture was directly purified over silica (hexanes to 1:1 hexanes EtOAc to 1:1 hexanes EtOAc+1% MeOH to 1:1 hexanes EtOAc+2% MeOH to 1:1 hexanes EtOAc+3% MeOH). The resulting compound was hydrolyzed according to General Procedure B to give the title compound. LCMS (m/z): 792.

Workup

  1. customThe reaction mixture was directly purified over silica (hexanes to 1:1 hexanes EtOAc to 1:1 hexanes EtOAc+1% MeOH to 1:1 hexanes EtOAc+2% MeOH to 1:1 hexanes EtOAc+3% MeOH)

Sources & evidence

ORD record
ord-ddaeafc570364be59d200dff837f060c
Source dataset
uspto-grants-2015_03
Patent number
US08987295B2

Reaction notes

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